Arylphenyl-substituted cyclic ketoenols

ABSTRACT

The present invention relates to novel arylphenyl-substituted cyclic ketoenols of the formula (I)  
                 
 
     in which  
     X represents halogen, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro, cyano or in each case optionally substituted phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio,  
     Y represents in each case optionally substituted cycloalkyl, aryl or hetaryl,  
     Z represents hydrogen, halogen, alkyl, alkoxy, alkenyloxy, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano,  
     CKE represents one of the groups  
                 
 
      in which  
     A, B. D, G and Q 1  to Q 6  are each as defined in the description,  
     to a plurality of processes for their preparation and to their use as pesticides and herbicides.

[0001] The present invention relates to novel arylphenyl-substitutedcyclic ketoenols, to a plurality of processes for their preparation andto their use as pesticides and herbicides.

[0002] Pharmaceutical properties of 3-acyl-pyrrolidine-2,4-diones havealready been described (S. Suzuki et al. Chem. Pharm. Bull. 15 1120(1967)). Furthermore, N-phenylpyrrolidine-2,4-diones have beensynthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem.1985, 1095). A biological activity of these compounds has not beendescribed.

[0003] EP-A-0 262 399 and GB-A-2 266 888 disclose compounds of a similarstructure (3-aryl-pyrrolidine-2,4-diones) of which, however, noherbicidal, insecticidal or acaricidal activity has become known.Unsubstituted bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives(EP-A-355 599 and EP-415 211) and substituted monocyclic3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-442 077)having herbicidal, insecticidal or acaricidal activity are known.

[0004] Also known are polycyclic 3-arylpyrrolidine-2,4-dione derivatives(EP-442 073) and 1H-arylpyrrolidine-dione derivatives (EP-456 063,EP-521 334, EP-596 298, EP-613 884, EP-613 885, WO 94/01 997, WO 95/26954, WO 95120572, EP-A-0 668 267, WO 96/25 395, WO 96/35 664, WO 97/01535, WO 97/02 243 and WO 97/36 868, WO 98/05 638).

[0005] It is known that certain substituted Δ³-dihydrofuran-2-onederivatives have herbicidal properties (cf. DE-A-4 014 420). Thesynthesis of the tetronic acid derivatives used as starting materials(such as, for example,3-(2-methyl-phenyl)-4-hydroxy-5-(4fluorophenyl)-Δ³-dihydrofuran-2-one)is likewise described in DE-A-4 014 420. Compounds of a similarstructure are known from the publication Campbell et al., J. Chem. Soc.,Perkin Trans. 1, 1985, (8) 1567-76, without any insecticidal and/oracaricidal activity being mentioned. Furthermore,3-aryl-Δ³-dihydrofuranone derivatives having herbicidal, acaricidal andinsecticidal properties are known from EP-A-528 156, EP-A-0 647 637, WO95/26 345, WO 96/20 196, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO97/02 243 and WO 97/36 868, WO 98/05 638. 3-Aryl-Δ³-dihydrothiophene-onederivatives are likewise known (WO 95/26 345, 96/25 395, WO 97/01 535,WO 97/02 243, WO 97/36 868, WO 98/05 638).

[0006] Also known from the literature are certain 3H-pyrazol-3-onederivatives, such as, for example,1,2-diethyl-1,2-dihydro-5-hydroxy4-phenyl-3H-pyrazol-3-one or[5-oxo-1,2-diphenyl-4-(p-sulphophenyl)-3-pyrazolin-3-yl]-oxy, disodiumsalt, orp-(3-hydroxy-5-oxo-1,2-diphenyl-3-pyrazolin4-yl)-benzenesulphonic acid(cf. J. Heterocycl. Chem., 25(5), 1301-1305, 1988 or J. Heterocycl.Chem., 25(5), 1307-1310, 1988 or Zh. Obshch. Khim., 34(7), 2397-2402,1964). However, a biological activity of these compounds is notdescribed.

[0007] Furthermore, it is known that the trisodium salt of4,4′,4″-(5-hydroxy-3-oxo-1H-pyrazol-1,2,4(3H)-triyl)-tris-benzenesulphonicacid has pharmacological properties (cf. Farmakol. Toksikol. (Moscow),38(2), 180-186, 1976). However, it is not known to be used in cropprotection.

[0008] Moreover, EP-508 126 and WO 92/16 510, WO 96/21 652 describe4-arylpyrazolidin-3,5-dione derivatives having herbicidal, acaricidaland insecticidal properties. Additionally, 4-arylpyrazolidines havebecome known of which fungicidal properties have been described (WO96/36 229, WO 96/36 615, WO 96/36 616, WO 96/36 633).

[0009] Certain phenyl-pyrone derivatives which are unsubstituted in thephenyl ring have already become known (cf. A. M. Chirazi, T. Kappe andE. Ziegler, Arch. Pharm. 309, 558 (1976) and K.-H. Boltze and K.Heidenbluth, Chem. Ber. 91, 2849), a possible use of these compounds aspesticides not being mentioned. Phenyl-pyrone derivatives which aresubstituted in the phenyl ring and have herbicidal, acaricidal andinsecticidal properties are described in EP-A-588 137, WO 96/25 395, WO96/35 664, WO 97/01 535, WO 97/02 243, WO 97/16 436, WO 97/19 941 and WO97/36 868, WO 98/05 638.

[0010] Certain 5-phenyl-1,3-thiazine derivatives which are unsubstitutedin the phenyl ring have already become known (cf. E. Ziegler and E.Steiner, Monatsh. 95, 147 (1964), R. Ketcham, T. Kappe and E. Ziegler,J. Heterocycl. Chem. 10, 223 (1973)), a possible use of these compoundsas pesticides not being mentioned. 5-Phenyl-1,3-thiazine derivativeswhich are substituted in the phenyl ring and have herbicidal, acaricidaland insecticidal activity are described in WO 94/14 785, WO 96/02 539,WO 96/35 664, WO 97/01,535, WO 97/02 243, WO 97/02 243, WO 97/36 868.

[0011] It is known that certain substituted 2-arylcyclopentanedioneshave herbicidal and acaricidal properties (cf., for example, U.S. Pat.Nos. 4,283,348; 4,338,122; 4,436,666; 4,526,723; 4,551,547; 4,632,698;WO 96/01798; WO 96/03366 and also WO 97/14667). Moreover, compounds of asimilar structure are known:3-hydroxy-5,5-dimethyl-2-phenylcyclopent-2-ene-1-one from thepublication Micklefield et al., Tetrahedron, (1992), 7519-26 and thenatural product involutine(−)-cis-5-(3,4-dihydroxyphenyl)-3,4-dihydroxy-2-(4-hydroxyphenyl)-cyclopent-2-ene-onefrom the publication Edwards et al., J. Chem. Soc. S, (1967), 405-9. Aninsecticidal or acaricidal activity is not described. Moreover,2-(2,4,6-trimethylphenyl)-1,3-indanedione is known from the publicationJ. Economic Entomology, 66, (1973), 584 and the Offenlegungsschrift DE-2361 084, with herbicidal and acaricidal activities being mentioned.

[0012] It is known that certain substituted 2-arylcyclohexanediones haveherbicidal and acaricidal properties (cf., for example, U.S. Pat. Nos.4,175,135, 4,209,432, 4,256,657, 4,256,658, 4,256,659, 4,257,858,4,283,348, 4,303,669, 4,351,666, 4,409,153, 4,436,666, 4,526,723,4,613,617, 4,659,372, DE-2,813,341, and also Wheeler, T. N., J. Org.Chem. 44, 4906 (1979)).

[0013] However, the activity and the activity spectrum of thesecompounds are, in particular at low application rates andconcentrations, not always entirely satisfactory. Furthermore, thecompatibility of these compounds with plants is not always satisfactory.

[0014] This invention, accordingly, provides novel compounds of theformula (I)

[0015] in which

[0016] X represents halogen, alkyl, alkoxy, alkenyloxy, alkylthio,alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkoxy,halogenoalkenyloxy, nitro, cyano or in each case optionally substitutedphenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio,

[0017] Y represents in each case optionally substituted cycloalkyl, arylor hetaryl,

[0018] Z represents hydrogen, halogen, alkyl, alkoxy, alkenyloxy,halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano,

[0019] CKE represents one of the groups

[0020]  in which

[0021] A represents hydrogen, in each case optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl,alkylthioalkyl, saturated or unsaturated, optionally substitutedcycloalkyl in which optionally at least one ring atom is replaced by aheteroatom, or in each case optionally halogen-, alkyl-, halogenoalkyl-,alkoxy, halogenoalkoxy-, cyano- or nitro-substituted aryl, arylalkyl orhetaryl,

[0022] B represents hydrogen, alkyl or alkoxyalkyl, or

[0023] A and B together with the carbon atom to which they are attachedrepresent a saturated or unsaturated unsubstituted or substituted cyclewhich optionally contains at least one heteroatom,

[0024] D represents hydrogen or an optionally substituted radicalselected from the series consisting of alkyl, alkenyl, alkinyl,alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturatedcycloalkyl in which one or more ring members are optionally replaced byheteroatoms, arylalkyl, aryl, hetarylalkyl or hetaryl or

[0025] A and D together with the atoms to which they are attachedrepresent a saturated or unsaturated cycle which is unsubstituted orsubstituted in the A,D moiety and which optionally contains at least one(in the case where CKE=(4) further) heteroatom, or

[0026] A and Q¹ together represent alkanediyl or alkenediyl, each ofwhich is optionally substituted by in each case optionally substitutedalkyl, hydroxyl, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl, or

[0027] Q¹ represents hydrogen or alkyl,

[0028] Q², Q⁴, Q⁵ and Q⁶ independently of one another each representhydrogen or alkyl,

[0029] Q³ represents hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl,optionally substituted cycloalkyl (in which optionally one methylenegroup is replaced by oxygen or sulphur) or optionally substitutedphenyl, or

[0030] Q³ and Q⁴ together with the carbon atom to which they areattached represent a saturated or unsaturated unsubstituted orsubstituted cycle which optionally contains a heteroatom,

[0031] G represents hydrogen (a) or represents one of the groups

[0032]  in which

[0033] E represents a metal ion or an ammonium ion,

[0034] L represents oxygen or sulphur,

[0035] M represents oxygen or sulphur,

[0036] R¹ represents in each case optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionallyhalogen-, alkyl- or alkoxy-substituted cycloalkyl, in which one or moremethylene groups can be replaced with heteroatoms, in each caseoptionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl orhetaryloxyalkyl,

[0037] R² represents in each case optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each caseoptionally substituted cycloalkyl, phenyl or benzyl,

[0038] R³, R⁴ and R⁵ independently of one another each represent in eachcase optionally halogen-substituted alkyl, alkoxy, alkylamino,dialkylamino, alkylthio, alkenylthio, cycloalkylthio and represent ineach case optionally substituted phenyl, benzyl, phenoxy or phenylthio,

[0039] R⁶ and R⁷ independently of one another each represent hydrogen,in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl,alkoxy, alkoxyalkyl, represent optionally substituted phenyl, representoptionally substituted benzyl, or together with the nitrogen atom towhich they are attached represent a cycle which is optionallyinterrupted by oxygen or sulphur.

[0040] Depending, inter alia, on the nature of the substituents, thecompounds of the formula (I) can be present as geometrical and/oroptical isomers or mixtures of isomers in varying compositions, whichcan be separated, if desired, in a customary manner. The presentinvention provides both the pure isomers and the isomer mixtures, theirpreparation and use and also compositions comprising them. In thefollowing, for simplicity, however, compounds of the formula (I) arealways referred to, although both pure compounds and, if appropriate,mixtures having different proportions of isomeric compounds areintended.

[0041] Including the meanings (1) to (8) of the group CKE, the followingprincipal structures (I-1) to (I-8) result:

[0042] in which

[0043] A, B, D, G, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each asdefined above.

[0044] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-1-a) to(I-1-g), result if CKE represents the group (1),

[0045] in which

[0046] A, B, D, E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are eachas defined above.

[0047] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-2-a) to(I-2-g), result if CKE represents the group (2),

[0048] in which

[0049] A, B, E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

[0050] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-3-a) to(I-3-g), result if CKE represents the group (3),

[0051] in which

[0052] A, B, E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

[0053] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-4-a) to(I-4-g), result if CKE represents the group (4),

[0054] in which

[0055] A, D, E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

[0056] Depending on the position of the substituent G, the compounds ofthe formula (I-5) can be present in the two isomeric forms of theformulae (I-5-A) and (I-5-B),

[0057] which is meant to be indicated by the dashed line in the formula(I-5).

[0058] The compounds of the formulae (I-5-A) and (I-5-B) can be presentboth as mixtures and in the form of their pure isomers. Mixtures of thecompounds of the formulae (I-5-A) and (I-5-B) can be separated, ifdesired, in a manner known per se by physical methods, for example bychromatographic methods.

[0059] For reasons of clarity, hereinbelow in each case only one of thepossible isomers is given. This does not exclude that the compounds may,if appropriate, be present in the form of the isomer mixtures or in therespective other isomeric form.

[0060] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-5-a) to(I-5-g) result if CKE represents the group (5),

[0061] in which

[0062] A, D, E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

[0063] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-6-a) to(I-6-g), result if CKE represents the group (6),

[0064] in which

[0065] A, E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

[0066] Depending on the position of the substituent G, the compounds ofthe formula (I-7) can be present in the two isomeric forms of theformulae (I-7-A) and (I-7-B):

[0067] which is meant to be indicated by the dashed line in the formula(I).

[0068] The compounds of the formulae (I-7-A) and (I-7-B) can be presentboth as mixtures and in the form of their pure isomers. Mixtures of thecompounds of the formulae (I-7-A) and (I-7-B) can be separated, ifdesired, by physical methods, for example by chromatographic methods.

[0069] For reasons of clarity, hereinbelow in each case only one of thepossible isomers is given. This does not exclude that the compounds may,if appropriate, be present in the form of the isomer mixtures or in therespective other isomeric form.

[0070] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-7-a) to(I-7-g) result:

[0071] in which

[0072] A, B, Q¹, Q², E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ areeach as defined above.

[0073] Depending on the position of the substituent G, the compounds ofthe formula (I-8) can be present in the two isomeric forms of theformulae (I-8-A) and (I-8-B)

[0074] which is meant to be indicated by the dashed line in the formula(I).

[0075] The compounds of the formulae (I-8-A) and (I-8-B) can be presentboth as mixtures and in the form of their pure isomers. Mixtures of thecompounds of the formulae (I-8-A) and (I-8-B) can be separated, ifdesired, by physical methods, for example by chromatographic methods.

[0076] For reasons of clarity, hereinbelow in each case only one of thepossible isomers is given. This takes into account that the relevantcompound may, if appropriate, be present as an isomer mixture or in therespective other isomeric form.

[0077] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-8-a) to(I-8-g) result:

[0078] in which

[0079] A, B, E, L, M, Q³, Q⁴, Q⁵, Q⁶, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶and R⁷ are each as defined above.

[0080] Furthermore, it has been found that the novel compounds of theformula (I) are obtained by one of the processes described below:

[0081] (A) Substituted 3-phenylpyrrolidine-2,4-diones or their enols ofthe formula (I-1-a)

[0082]  in which

[0083] A, B, D, X, Y and Z are each as defined above

[0084] are obtained when

[0085] N-acylamino acid esters of the formula (II)

[0086]  in which

[0087] A, B, D, X, Y and Z are each as defined above

[0088] and

[0089] R⁸ represents alkyl (preferably C₁-C₆-alkyl)

[0090] are condensed intramolecularly in the presence of a diluent andin the presence of a base.

[0091] (B) Moreover, it has been found that substituted3-phenyl-4-hydroxy-Δ³-dihydrofuranone derivatives of the formula (I-2-a)

[0092]  in which

[0093] A, B, X, Y and Z are each as defined above

[0094] are obtained when

[0095] carboxylic esters of the formula (III)

[0096]  in which

[0097] A, B, X, Y, Z and R⁸ are each as defined above

[0098] are condensed intramolecularly in the presence of a diluent andin the presence of a base.

[0099] (C) Furthermore, it has been found that substituted3-phenyl-4-hydroxy-Δ³-dihydrothiophenone derivatives of the formula(I-3-a)

[0100]  in which

[0101] A, B, X, Y and Z are each as defined above

[0102] are obtained when

[0103] β-ketocarboxylic esters of the formula (IV)

[0104]  in which

[0105] A, B, X, Y, Z and R⁸ are each as defined above and

[0106] W represents hydrogen, halogen (preferably fluorine, chlorine,bromine), alkyl (preferably C₁-C₆-alkyl) or alkoxy (preferablyC₁-C₈-alkoxy)

[0107] are cyclized intramolecularly, if appropriate in the presence ofa diluent and in the presence of an acid.

[0108] (D) Furthermore, substituted3-hydroxyl-4-phenyl-5-oxo-pyrazolines of the formula (I-4-a)

[0109]  in which

[0110] A, D, X, Y and Z are each as defined above

[0111] are obtained when

[0112] (α) halogenocarbonyl ketenes of the formula (V)

[0113]  in which

[0114] X, Y and Z are each as defined above

[0115] and

[0116] Hal represents halogen (in particular chlorine or bromine)

[0117] or

[0118] (β) malonic acid derivatives of the formula (VI)

[0119]  in which

[0120] R⁸, X, Y and Z are each as defined above

[0121] are reacted with hydrazines of the formula (VII)

A-NH-NH-D  (VII)

[0122]  in which

[0123] A and D are each as defined above

[0124] if appropriate in the presence of a diluent and if appropriate inthe presence of a base.

[0125] (E) Furthermore, it has been found that the novel substituted3-phenylpyrone derivatives of the formula (I-5-a)

[0126]  in which

[0127] A, D, X, Y and Z are each as defined above

[0128] are obtained when

[0129] carbonyl compounds of the formula (VIII)

[0130]  in which

[0131] A and D are each as defined above

[0132] or their silyl enol ethers of the formula (VIIIa)

[0133]  in which

[0134] A, D and R⁸ are each as defined above

[0135] are reacted with ketene acid halides of the formula (V)

[0136]  in which

[0137] X, Y and Z are each as defined above and

[0138] Hal represents halogen (preferably represents chlorine orbromine),

[0139] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid acceptor.

[0140] Furthermore, it has been found

[0141] (F) that the novel substituted phenyl-1,3-thiazine derivatives ofthe formula (I-6-a)

[0142]  in which

[0143] A, X, Y and Z are each as defined above

[0144] are obtained when thioamides of the formula (IX)

[0145]  in which

[0146] A is as defined above

[0147] are reacted with ketene acid halides of the formula (V)

[0148]  in which

[0149] Hal, X, Y and Z are each as defined above,

[0150] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid acceptor.

[0151] Furthermore, it has been found

[0152] (G) that compounds of the formula (I-7-a)

[0153]  in which

[0154] A, B, Q¹, Q², X, Y and Z are each as defined above

[0155] are obtained when

[0156] ketocarboxylic esters of the formula (X)

[0157]  in which

[0158] A, B, Q¹, Q², X, Y and Z are each as defined above and

[0159] R⁸ represents alkyl (in particular C₁-C₈-alkyl)

[0160] are cyclized intramolecularly, if appropriate in the presence ofa diluent and in the presence of a base.

[0161] Moreover, it has been found

[0162] (H) that compounds of the formula (I-8-a)

[0163]  in which

[0164] A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above

[0165] are obtained when

[0166] 6-aryl-5-keto-hexanoic esters of the formula (XI)

[0167]  in which

[0168] A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above

[0169] and

[0170] R⁸ represents alkyl (preferably C₁-C₆-alkyl)

[0171] are condensed intramolecularly in the presence of a diluent andin the presence of a base;

[0172] or

[0173] (I) that compounds of the formulae (I-1-a) to (I-8-a) shown abovein which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as definedabove are obtained when compounds of the formula (I-1′-a) to (I-8′-a),

[0174]  in which

[0175] A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X and Z are each as definedabove and

[0176] Y′ represents chlorine, bromine or iodine, preferably representsbromine,

[0177] are reacted with boronic acids of the formula (XII)

[0178]  in which

[0179] Y is as defined above

[0180] in the presence of a solvent, a base and a catalyst, suitablecatalysts being, in particular, palladium complexes.

[0181] Moreover, it has been found

[0182] (J) that the compounds of the formulae (I-1-b) to (I-8-b) shownabove in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, R¹, X, Y and Z are eachas defined above are obtained when compounds of the formulae (I-1-a) to(I-8-a) shown above in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Zare each as defined above are in each case

[0183] (α) reacted with acyl halides of the formula (XIII)

[0184]  in which

[0185] R¹ is as defined above and

[0186] Hal represents halogen (in particular chlorine or bromine)

[0187] or

[0188] (β) reacted with carboxylic anhydrides of the formula (XIV)

R¹—CO—O—CO—R¹  (XIV)

[0189]  in which

[0190] R¹ is as defined above,

[0191] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder;

[0192] (K) that the compounds of the formulae (I-1-c) to (I-8-c) shownabove in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, R², M, X, Y and Z areeach as defined above and L represents oxygen are obtained whencompounds of the formulae (I-1-a) to (I-8-a) shown above in which A, B,D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X,

[0193] Y and Z are each as defined above are in each case

[0194] reacted with chloroformic esters or chloroformic thioesters ofthe formula (XV)

R²-M-CO—Cl  (XV)

[0195]  in which

[0196] R² and M are each as defined above,

[0197] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder;

[0198] (L) that compounds of the formulae (I-1-c) to (I-8-c) shown abovein which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, R², M, X, Y and Z are each asdefined above and L represents sulphur are obtained when compounds ofthe formulae (I-1-a) to (I-8-a) shown above in which A, B, D, Q¹, Q²,Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above are in each case

[0199] reacted with chloromonothioformic esters or chlorodithioformicesters of the formula (XVI)

[0200]  in which

[0201] M and R² are each as defined above

[0202] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder

[0203] and

[0204] (M) that compounds of the formulae (I-1-d) to (I-8-d) shown abovein which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, R³, X, Y and Z are each asdefined above are obtained when compounds of the formulae (I-1-a) to(I-8-a) shown above in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Zare each as defined above are in each case

[0205] reacted with sulphonyl chlorides of the formula (XVII)

R³—SO₂—Cl  (XVII)

[0206]  in which

[0207] R³ is as defined above,

[0208] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder,

[0209] (N) that compounds of the formulae (I-1-e) to (I-8-e) shown abovein which A, B, D, L, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, R⁴, R⁵, X, Y and Z are eachas defined above are obtained when compounds of the formulae (I-1-a) to(I-8-a) shown above in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Zare each as defined above are in each case

[0210] reacted with phosphorus compounds of the formula (XVIII)

[0211]  in which

[0212] L, R⁴ and R⁵ are each as defined above and

[0213] Hal represents halogen (in particular chlorine or bromine),

[0214] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder,

[0215] (L) that compounds of the formulae (I-1-f) to (I-8-f) shown abovein which A, B, D, E, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each asdefined above are obtained when compounds of the formulae (I-1-a) to(I-8-a) in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each asdefined above are in each case

[0216] reacted with metal compounds or amines of the formulae (XIX) or(XX)

[0217]  in which

[0218] Me represents a mono- or divalent metal (preferably an alkalimetal or alkaline earth metal, such as lithium, sodium, potassium,magnesium or calcium),

[0219] t represents the number 1 or 2 and

[0220] R¹⁰, R¹¹, R¹² independently of one another each representhydrogen or alkyl (preferably C₁-C₈-alkyl),

[0221] if appropriate in the presence of a diluent,

[0222] (P) that compounds of the formulae (I-1-g) to (I-8-g) shown abovein which A, B, D, L, Q¹. Q², Q³, Q⁴, Q⁵, Q⁶, R⁶, R⁷, X, Y and Z are eachas defined above are obtained when compounds of the formulae (I-1-a) to(I-8-a) shown above in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Zare each as defined above are in each case

[0223] (α) reacted with isocyanates or isothiocyanates of the formula(XXI)

R⁶—N═C═L  (XXI)

[0224]  in which

[0225] R⁶ and L are each as defined above

[0226] if appropriate in the presence of a diluent and if appropriate inthe presence of a catalyst, or

[0227] (β) reacted with carbamoyl chlorides or thiocarbamoyl chloridesof the formula (XXII)

[0228]  in which

[0229] L, R⁶ and R⁷ are each as defined above

[0230] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder.

[0231] Furthermore, it has been found that the novel compounds of theformula (I) have very good activity as pesticides, preferably asinsecticides, acaricides and also as herbicides.

[0232] The formula (I) provides a general definition of the compoundsaccording to the invention. Preferred substituents or ranges of theradicals listed in the formulae mentioned hereinabove and hereinbeloware illustrated below:

[0233] X preferably represents halogen, C₁-C₆-alkyl,C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkoxy,C₃-C₆-halogenoalkenyloxy, nitro, cyano or in each case optionallyhalogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy,phenylthio, benzyloxy or benzylthio.

[0234] Y preferably represents one of the radicals

[0235] V¹ preferably represents hydrogen, halogen, C₁-C₁₂-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro, cyano orphenyl, phenoxy, phenoxy-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy,phenylthio-C₁-C₄-alkyl or phenyl-C₁-C₄-alkylthio, each of which isoptionally mono- or polysubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C_(l)-C₄-halogenoalkoxy, nitro orcyano.

[0236] V² and V³ independently of one another each preferably representhydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl orC₁-C₄-halo-genoalkoxy.

[0237] Z preferably represents hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy, nitro or cyano.

[0238] CKE preferably represents one of the groups

[0239] A preferably represents hydrogen or in each case optionallyhalogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₁-C₁₀-alkoxy-C₁-C₈-alkyl, poly-C₁-C₈-alkoxy-C₁-C₈-alkyl,C₁-C₁₀-alkylthio-C₁-C₆-alkyl, optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one or twonot directly adjacent ring members are replaced by oxygen and/or sulphuror represents in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano- ornitro-substituted C₆- or C₁₀-aryl (phenyl or naphthyl), hetaryl having 5to 6 ring atoms (for example furanyl, pyridyl, imidazolyl, triazolyl,pyrazolyl, pyrimidyl, thiazolyl or thienyl) or C₆- orC₁₀-aryl-C₁-C₆-alkyl (phenyl-C₁-C₆-alkyl or naphthyl- C₁-C₆-alkyl).

[0240] B preferably represents hydrogen, C₁-C₁₂-alkyl orC₁-C₈-alkoxy-C₁-C₆-alkyl or

[0241] A, B and the carbon atom to which they are attached preferablyrepresent saturated C₃-C₁₀-cycloalkyl or unsaturated C₅-C₁₀-cycloalkylin which optionally one ring member is replaced by oxygen or sulphur andwhich are optionally mono- or disubstituted by C₁-C₈-alkyl,C₃-C₁₀-cycloalkyl, C₁-C₈-halogeno-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio,halogen or phenyl or

[0242] A, B and the carbon atom to which they are attached preferablyrepresent C₃-C₆-cycloalkyl which is substituted by an alkylenedilylgroup which optionally contains one or two not directly adjacent oxygenand/or sulphur atoms, or by an alkylenedioxyl group or by analkylenedithioyl group which, together with the carbon atom to which itis attached, forms a further five- to eight-membered ring, or

[0243] A, B and the carbon atom to which they are attached preferablyrepresent C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl, in which twosubstituents together with the carbon atoms to which they are attachedrepresent in each case optionally C₁-C₆-alkyl-, C₁-C₆-alkoxy- orhalogen-substituted C₂-C₆-alkanediyl, C₂-C₆-alkenediyl orC₄-C₆-alkanedienediyl in which optionally one methylene group isreplaced by oxygen or sulphur.

[0244] D preferably represents hydrogen, in each case optionallyhalogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkinyl,C₁-C₁₀-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,C₁-C₁₀-alkylthio-C₂-C₈-alkyl, optionally halogen-, C₁-C₄-alkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkyl-substituted C₃-C₈-cycloalkyl inwhich optionally one ring member is replaced by oxygen or sulphur or ineach case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano- or nitro-substitutedphenyl, hetaryl having 5 or 6 ring atoms (for example furanyl,imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thienylor triazolyl), phenyl-C₁-C₆-alkyl or hetaryl-C₁-C₆-alkyl having 5 or 6ring atoms (for example furanyl-, imidazolyl-, pyridyl-, thiazolyl-,pyrazolyl-, pyrimidyl-, pyrrolyl-, thienyl- or triazolyl- C₁-C₆-alkyl),or

[0245] A and D together preferably represent in each case optionallysubstituted C₃-C₆-alkanediyl or C₃-C₆-alkenediyl in which optionally onemethylene group is replaced by oxygen or sulphur,

[0246]  possible substituents in each case being:

[0247] halogen, hydroxyl, mercapto or in each case optionallyhalogen-substituted C₁-C₁₀-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₃-C₇-cycloalkyl, phenyl or benzyloxy, or a further C₃-C₆-alkanediylgrouping, C₃-C₆-alkenediyl grouping or a butadienyl grouping which isoptionally substituted by C₁-C₆-alkyl or in which optionally twoadjacent substituents together with the carbon atoms to which they areattached form a further saturated or unsaturated cycle having 5 or 6ring atoms (in the case of the compound of the formula (I-1), A and D,together with the atoms to which they are attached, then represent, forexample, the groups AD-1 to AD-10 mentioned further below) which cyclemay contain oxygen or sulphur, or which may optionally contain one ofthe groups below

[0248] A and Q¹ together preferably represent C₃-C₆-alkanediyl orC₄-C₆-alkenediyl, each of which is optionally mono- or disubstituted byidentical or different substituents selected from the group consistingof halogen, hydroxyl; C₁-C₁₀-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₃-C₇-cycloalkyl, each of which is optionally mono- to trisubstituted byidentical or different halogens; and benzyloxy and phenyl, each of whichis optionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen, C₁-C₆-alkylor C₁ -C₆-alkoxy, and which furthermore optionally contains one of thegroups below

[0249]  or is bridged by a C₁-C₂-alkanediyl group or by an oxygen atom,or

[0250] Q¹ preferably represents hydrogen or C₁-C₄-alkyl.

[0251] Q², Q⁴, Q⁵ and Q⁶ independently of one another each preferablyrepresent hydrogen or C₁-C₄-alkyl,

[0252] Q³ preferably represents hydrogen, C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₂-alkyl, C₁-C₆-alkylthio-C₁-C₂-alkyl, optionallyC₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in whichoptionally one methylene group is replaced by oxygen or sulphur oroptionally halogen-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, cyano- or nitro-substituted phenyl, or

[0253] Q³ and Q⁴ together with the carbon atom to which they areattached represent optionally C₁-C₄-alkyl-, C₁-C₄-alkoxy- orC₁-C₂-halogenoalkyl-substituted C₃-C₇-cycloalkyl in which optionally onering member is replaced by oxygen or sulphur.

[0254] G preferably represents hydrogen (a) or represents one of thegroups

[0255]  in particular represents (a), (b) or (c),

[0256] in which

[0257] E represents a metal ion or an ammonium ion,

[0258] L represents oxygen or sulphur and

[0259] M represents oxygen or sulphur.

[0260] R¹ preferably represents in each case optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl,poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or optionally halogen-, C₁-C₆-alkyl-orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one ormore (preferably one or two) not directly adjacent ring members arereplaced by oxygen and/or sulphur,

[0261] represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-, C₁-C₆-halo genoalkoxy-,C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl,

[0262] represents optionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl,

[0263] represents optionally halogen- or C₁-C₆-alkyl-substituted 5- or6-membered hetaryl (for example pyrazolyl, thiazolyl, pyridyl,pyrimidyl, furanyl or thienyl),

[0264] represents optionally halogen- or C₁-C₆-alkyl-substitutedphenoxy-C₁-C₆-alkyl or

[0265] represents optionally halogen-, amino- or C₁-C₆-alkyl-substituted5- or 6-membered hetaryloxy-C₁-C₆-alkyl (for examplepyridyloxy-C₁-C₆-alkyl, pyrimidyloxy-C₁-C₆-alkyl orthiazolyloxy-C₁-C₆-alkyl).

[0266] R² preferably represents in each case optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,

[0267] represents optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl or

[0268] represents in each case optionally halogen-, cyano-, nitro-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- orC₁-C₆-halogenoalkoxy-substituted phenyl or benzyl.

[0269] R³ preferably represents optionally halogen-substitutedC₁-C₈-alkyl or represents in each case optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl.

[0270] R⁴ and R⁵ independently of one another each preferably representin each case optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamnino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio,C₂-C₈-alkenylthio, C₃-C₇-cycloalkylthio or represent in each caseoptionally halogen-, nitro-, cyano-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkyl- or C₁-C₄-halogenoalkyl-substituted phenyl, phenoxy orphenylthio.

[0271] R⁶ and R⁷ independently of one another each preferably representhydrogen, represent in each case optionally halogen-substitutedC₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, represent optionally halogen-,C₁-C₈-halogenoalkyl-, C₁-C₈-alkyl- or C₁-C₈-alkoxy-substituted phenyl,optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- orC₁-C₈-alkoxy-substituted benzyl or together represent an optionallyC₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally onecarbon atom is replaced by oxygen or sulphur.

[0272] R¹³ preferably represents hydrogen, represents in each caseoptionally halogen-substituted C₁-C₈-alkyl or C₁-C₈-alkoxy, representsoptionally halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substitutedC₃-C₈-cycloalkyl in which optionally one methylene group is replaced byoxygen or sulphur, or represents in each case optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl,phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkoxy.

[0273] R¹⁴ preferably represents hydrogen or C₁-C₈-alkyl, or

[0274] R¹³ and R¹⁴ together preferably represent C₄-C₆-alkanediyl.

[0275] R¹⁵ and R¹⁶ are identical or different and each preferablyrepresent C₁-C₆-alkyl, or

[0276] R¹⁵ and R¹⁶ together preferably represent a C₂-C₄-alkanediylradical which is optionally substituted by C₁-C₆-alkyl,C₁-C₆-halogenoalkyl or by optionally halogen-, C₁-C₆-alkyl-,C₁-C₄-halogenoalkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkoxy-, nitro- orcyano-substituted phenyl.

[0277] R¹⁷ and R¹⁸ independently of one another each preferablyrepresent hydrogen, represent optionally halogen-substituted C₁-C₈-alkylor represent optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, or

[0278] R¹⁷ and R¹⁸ together with the carbon atom to which they areattached preferably represent a carbonyl group or represent optionallyhalogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₅-C₇-cycloalkyl inwhich optionally one methylene group is replaced by oxygen or sulphur.

[0279] R¹⁹ and R²⁰ independently of one another each preferablyrepresent C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₁-C₁₀-alkoxy,C₁-C₁₀-alkylamino, C₃-C₁₀-alkenylamino, di-(C₁-C₁₀-alkyl)amino ordi-(C₃-C₁₀-alkenyl)amino.

[0280] In the preferred radical definitions, halogen, including assubstituent, such as, for example, in halogenoalkyl, representsfluorine, chlorine, bromine and iodine and in particular representsfluorine and chlorine.

[0281] X particularly preferably represents fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, C₃-C₄-halogenoalkenyloxy, nitro or cyano.

[0282] Y particularly preferably represents one of the radicals

[0283] V¹ particularly preferably represents hydrogen, fluorine,chlorine, bromine, C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro, cyano or phenyl, phenoxy,phenoxy-C₁-C₂-alkyl, phenyl-C₁-C₂-alkoxy, phenylthio-C₁-C₂-alkyl orphenyl-C₁-C₂-alkylthio, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, nitro or cyano.

[0284] V² and V³ independently of one another each particularlypreferably represent hydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl or C₁-C₂-halogenoalkoxy.

[0285] Z particularly preferably represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy orC₁-C₄-halogenoalkoxy.

[0286] CKE particularly preferably represents one of the groups

[0287] A particularly preferably represents hydrogen, in each caseoptionally fluorine-or chlorine-substituted C₁-C₁₀-alkyl,C₁-C₈-alkoxy-C₁-C₆-alkyl, optionally fluorine-, chlorine-, C₁-C₄-alkyl-or C₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl in which optionally onering member is replaced by oxygen or sulphur or (but not in the case ofthe compounds of the formulae (I-5), (I-7) and (I-8)) in each caseoptionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substitutedphenyl, furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl,thiazolyl, thienyl or phenyl-C₁-C₄-alkyl.

[0288] B particularly preferably represents hydrogen or C₁-C₆-alkyl, or

[0289] A, B and the carbon atom to which they are attached particularlypreferably represent saturated or unsaturated C₅-C₇-cycloalkyl in whichoptionally one ring member is replaced by oxygen or sulphur and which isoptionally monosubstituted by C₁-C₆-alkyl, C₅-C₈-cycloalkyl,C₁-C₃-halogenoalkyl, C₁-C₆-alkoxy, fluorine, chlorine or phenyl, or

[0290] A, B and the carbon atom to which they are attached particularlypreferably represent C₅-C₆-cycloalkyl which is substituted by analkylenediyl group which optionally contains one or two not directlyadjacent oxygen or sulphur atoms or by an alkylenedioxyl group or by analkylenedithiol group which, together with the carbon atom to which itis attached, forms a further five- or six-membered ring, or

[0291] A, B and the carbon atom to which they are attached particularlypreferably represent C₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in which twosubstituents together with the carbon atoms to which they are attachedrepresent in each case optionally C₁-C₅-alkyl-, C₁-C₅-alkoxy-,fluorine-, chlorine- or bromine-substituted C₂-C₄-alkanediyl,C₂-C₄-alkenediyl, in which optionally one methylene group is replaced byoxygen or sulphur, or butadienediyl.

[0292] D particularly preferably represents hydrogen, represents in eachcase optionally fluorine- or chlorine-substituted C₁-C₁₀-alkyl,C₃-C₆-alkenyl, C₁-C₈-alkoxy-C₂-C₆-alkyl or C₁-C₈-alkylthio-C₂-C₆-alkyl,represents optionally fluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-or C₁-C₂-halogenoalkyl-substituted C₃-C₇-cycloalkyl in which optionallyone methylene group is replaced by oxygen or sulphur or (but not in thecase of the compounds of the formulae (I-1) and (I-4)) represents ineach case optionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substitutedphenyl, furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl,pyrrolyl, thienyl, triazolyl or phenyl-C₁-C₄-alkyl, or

[0293] A and D together particularly preferably represent optionallysubstituted C₃-C₅-alkanediyl in which one methylene group may bereplaced by a carbonyl group, oxygen or sulphur, possible substituentsbeing hydroxyl, C₁-C₆-alkyl or C₁-C₄-alkoxy, or

[0294] A and D (in the case of the compounds of the formula (I-1))together with the atoms to which they are attached represent one of thegroups AD-1 to AD-10:

[0295]  or

[0296] A and Q¹ together particularly preferably representC₃-C₄-alkanediyl or C₃-C₄-alkenediyl, each of which is optionally mono-or disubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, hydroxyl, and C₁-C₈-alkyland C₁-C₄-alkoxy, each of which is optionally mono- to trisubstituted byfluorine, or

[0297] Q¹ particularly preferably represents hydrogen.

[0298] Q² particularly preferably represents hydrogen.

[0299] Q⁴, Q⁵ and Q⁶ independently of one another each particularlypreferably represent hydrogen or C₁-C₃-alkyl.

[0300] Q³ particularly preferably represents hydrogen, C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl or optionallymethyl- or methoxy-substituted C₃-C₆-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur, or

[0301] Q³ and Q⁴ together with the carbon atom to which they areattached particularly preferably represent an optionally C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted saturated C₅-C₆-cycloalkyl in which optionallyone ring member is replaced by oxygen or sulphur.

[0302] G particularly preferably represents hydrogen (a) or particularlypreferably represents one of the groups

[0303]  in particular represents (a), (b) or (c),

[0304] in which

[0305] E represents a metal ion or an ammonium ion,

[0306] L represents oxygen or sulphur and

[0307] M represents oxygen or sulphur.

[0308] R¹ particularly preferably represents in each case optionallyfluorine- or chlorine-substituted C₁-C₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl,poly-C₁-C₆-alkoxy-C₁-C₆-alkyl or optionally fluorine-, chlorine-,C₁-C₅-alkyl- or C₁-C₅-alkoxy-substituted C₃-C₇-cycloalkyl in whichoptionally one or two not directly adjacent ring members are replaced byoxygen and/or sulphur,

[0309] represents optionally fluorine-, chlorine-, bromine-, cyano-,nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl-,C₁-C₃-halogenoalkoxy-, C₁-C₄-alkylthio- orC₁-C₄-alkylsulphonyl-substituted phenyl,

[0310] represents optionally fluorine-, chlorine-, bromine-,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl- orC₁-C₃-halogenoalkoxy-substituted phenyl-C₁-C₄-alkyl,

[0311] represents in each case optionally fluorine-, chlorine-, bromine-or C₁-C₄-alkyl-substituted pyrazolyl, thiazolyl, pyridyl, pyrimidyl,furanyl or thienyl,

[0312] represents optionally fluorine-, chlorine-, bromine- orC₁-C₄-alkyl-substituted phenoxy-C₁-C₃-alkyl or

[0313] represents in each case optionally fluorine-, chlorine-,bromine-, amino- or C₁-C₄-alkyl-substituted pyridyloxy-C₁-C₃-alkyl,pyrimidyloxy-C₁-C₃-alkyl or thiazolyloxy-C₁-C₃-alkyl.

[0314] R² particularly preferably represents in each case optionallyfluorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₂-C₆-alkyl or poly-C₁-C₆-alkoxy-C₂-C₆-alkyl,

[0315] represents optionally fluorine-, chlorine-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl or

[0316] represents in each case optionally fluorine-, chlorine-,bromine-, cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₃-alkoxy-,C₁-C₃-halogenoalkyl- or C₁-C₃-halo-genoalkoxy-substituted phenyl orbenzyl,

[0317] R³ particularly preferably represents optionallyfluorine-substituted C₁-C₆-alkyl or particularly preferably representsin each case optionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl-, C₁-C₃-halogenoalkoxy-, cyano- ornitro-substituted phenyl or benzyl,

[0318] R⁴ and R⁵ independently of one another each particularlypreferably represent C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio, C₃-C₄-alkenylthio,C₃-C₆-cycloalkylthio or represent in each case optionally fluorine-,chlorine-, bromine-, nitro-, cyano-, C₁-C₃-alkoxy-,C₁-C₃-halogenoalkoxy-, C₁-C₃-alkylthio-, C₁-C₃-halogenoalkylthio-,C₁-C₃-alkyl- or C₁ -C₃-halogenoalkyl-substituted phenyl, phenoxy orphenylthio, and

[0319] R⁶ and R⁷ independently of one another each particularlypreferably represent hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, representoptionally fluorine-, chlorine-, bromine-, C₁-C₃-halogenoalkyl-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted phenyl, represent optionallyfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₃-halogenoalkyl- orC₁-C₄-alkoxy-substituted benzyl, or together represent an optionallymethyl- or ethyl-substituted C₄-C₅-alkylene radical in which optionallyone methylene group is replaced by oxygen or sulphur.

[0320] In the particularly preferred radical definitions, halogen,including as substituent, such as, for example, in halogenoalkyl,represents fluorine, chlorine, bromine and iodine, in particularrepresents fluorine, chlorine and bromine and very particularlyrepresents fluorine or chlorine.

[0321] X very particularly preferably represents fluorine, chlorine,methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, n-propoxy,iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitroor cyano (with emphasis on fluorine, chlorine, methyl, ethyl, n-propylor iso-propyl).

[0322] Y very particularly preferably represents one of the radicals

[0323] V¹ very particularly preferably represents hydrogen, fluorine,chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, n-butyl,iso-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy,trifluoromethyl, trifluoromethoxy, nitro, cyano or phenyl.

[0324] V² and V³ independently of one another each very particularlypreferably represent hydrogen, fluorine, chlorine, methyl, ethyl,n-propyl, iso-propyl, methoxy, ethoxy, trifluoromethyl ortrifluoromethoxy.

[0325] Z very particularly preferably represents hydrogen, fluorine,chlorine, methyl, ethyl, n-propyl, methoxy, ethoxy or n-propoxy (withemphasis on hydrogen, fluorine, chlorine, methyl, ethyl or n-propyl).

[0326] CKE very particularly preferably represents one of the groups

[0327] A very particularly preferably represents hydrogen, in each caseoptionally fluorine-substituted C₁-C₈-alkyl or C₁-C₆-alkoxy-C₁-C₄-alkyl,optionally fluorine-, methyl-, ethyl- or methoxy-substitutedC₃-C₆-cycloalkyl in which optionally one ring member is replaced byoxygen or sulphur or (but not in the case of the compounds of theformulae (I-5), (I-7) and (I-8)) represents in each case optionallyfluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, iso-propyl-,methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- ornitro-substituted phenyl or benzyl.

[0328] B very particularly preferably represents C₁-C₄-alkyl, or

[0329] A, B and the carbon atom to which they are attached veryparticularly preferably represent saturated C₅-C₆-cycloalkyl in whichoptionally one ring member is replaced by oxygen or sulphur and which isoptionally monosubstituted by methyl, ethyl, n-propyl, isopropyl, butyl,iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, methoxy, ethoxy,n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy,fluorine or chlorine, or

[0330] A, B and the carbon atom to which they are attached veryparticularly preferably represent C₅-C₆-cycloalkyl in which twosubstituents together with the carbon atoms to which they are attachedrepresent C₂-C₄-alkanediyl or C₂-C₄-alkenediyl in which in each caseoptionally one methylene group is replaced by oxygen or sulphur, orbutadienediyl.

[0331] D very particularly preferably represents hydrogen, represents ineach case optionally fluorine- or chlorine-substituted C₁-C₈-alkyl,C₃-C₄-alkenyl, C₁-C₆-alkoxy-C₂-C₄-alkyl, C₁-C₄-alkylthio-C₂-C₄-alkyl orC₃-C₆-cycloalkyl in which optionally one methylene group is replaced byoxygen or sulphur or (but not in the case of the compounds of theformulae (I-1) and (I-4)) represents in each case optionally fluorine-,chlorine-, methyl-, ethyl-, n-propyl-, iso-propyl-, methoxy-, ethoxy-,trifluoromethyl- or trifluoromethoxy-substituted phenyl, furanyl,pyridyl, thienyl or benzyl (in compounds of the formula (I-1) withemphasis on hydrogen),

[0332] or

[0333] A and D together very particularly preferably representoptionally substituted C₃-C₄-alkanediyl in which optionally one carbonatom is replaced by sulphur and which is optionally substituted byhydroxyl, methyl, ethyl, methoxy or ethoxy, or

[0334] A and D (in the case of the compounds of the formula (I-1))together with the atoms to which they are attached represent one of thefollowing groups AD:

[0335] A and Q¹ together very particularly preferably representC₃-C₄-alkanediyl or butenediyl, each of which is optionally mono- ordisubstituted by fluorine, hydroxyl, methyl or methoxy, or

[0336] Q¹ very particularly preferably represents hydrogen.

[0337] Q² very particularly preferably represents hydrogen.

[0338] Q⁴, Q⁵ and Q⁶ independently of one another each very particularlypreferably represent hydrogen, methyl or ethyl.

[0339] Q³ very particularly preferably represents hydrogen, methyl,ethyl or C₃-C₆-cycloalkyl in which optionally one methylene group isreplaced by oxygen or sulphur (with emphasis on hydrogen, methyl orethyl), or

[0340] Q³ and Q⁴ together with the carbon to which they are attachedvery particularly preferably represent optionally methyl- ormethoxy-substituted saturated C₅-C₆-cycloalkyl in which optionally onering member is replaced by oxygen or sulphur.

[0341] G very particularly preferably represents hydrogen (a) orrepresents one of the groups

[0342]  in particular represents (a), (b) or (c),

[0343] in which

[0344] E represents a metal ion or an ammonium ion,

[0345] L represents oxygen or sulphur and

[0346] M represents oxygen or sulphur.

[0347] R¹ very particularly preferably represents in each caseoptionally, fluorine- or chlorine-substituted C₁-C₁₄-alkyl,C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₁-C₆-alkyl, C₁-C₄-alkylthio-C₁-C₆-alkyl,poly-C₁-C₄-alkoxy-C₁-C₄-alkyl or optionally fluorine-, chlorine-,methyl-, ethyl-, n-propyl-, i-propyl-, n-butyl-, i-butyl-, tert-butyl-,methoxy-, ethoxy-, n-propoxy- or iso-propoxy-substitutedC₃-C₆-cycloalkyl in which optionally one or two not directly adjacentring members are replaced by oxygen and/or sulphur,

[0348] represents optionally fluorine-, chlorine-, bromine-, cyano-,nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-,trifluoromethyl-, trifluoromethoxy-, methylthio-, ethylthio-,methylsulphonyl- or ethylsulphonyl-substituted phenyl,

[0349] represents optionally fluorine-, chlorine-, bromine-, methyl-,ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- ortrifluoromethoxy-substituted benzyl,

[0350] represents in each case optionally fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted faranyl, thienyl, pyridyl,pyrimidyl, thiazolyl or pyrazolyl,

[0351] represents optionally fluorine-, chlorine-, methyl- orethyl-substituted phenoxy-C₁-C₂-alkyl or

[0352] represents in each case optionally fluorine-, chlorine-, amino-,methyl- or ethyl-substituted pyridyloxy-C₁-C₂-alkyl,pyrimidyloxy-C₁-C₂-alkyl or thiazolyloxy-C₁-C₂-alkyl.

[0353] R² very particularly preferably represents in each caseoptionally fluorine-substituted C₁-C₁₄-alkyl, C₂-C₁₄-alkenyl,C₁-C₄-alkoxy-C₂-C₆-alkyl or poly-C₁-C₄-alkoxy-C₂-C₆-alkyl,

[0354] represents optionally fluorine-, chlorine-, methyl-, ethyl-,n-propyl-, isopropyl- or methoxy-substituted C₃-C₆-cycloalkyl,

[0355] or represents in each case optionally fluorine-, chlorine-,cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-,ethoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl orbenzyl.

[0356] R³ very particularly preferably represents in each caseoptionally fluorine-substituted methyl, ethyl, n-propyl, isopropyl or ineach case optionally fluorine-, chlorine-, bromine-, methyl-,tert-butyl-, methoxy-, trifluoro-methyl-, trifluoromethoxy-, cyano- ornitro-substituted phenyl or benzyl,

[0357] R⁴ and R⁵ independently of one another each very particularlypreferably represent C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,di-(C₁-C₄-alkyl)amino, C₁-C₄-alkylthio or represent in each caseoptionally fluorine-, chlorine-, bromine-, nitro-, cyano-,C₁-C₂-alkoxy-, C₁-C₂-fluoroalkoxy-, C₁-C₂-alkylthio-,C₁-C₂-fluoroalikylthio- or C₁-C₃-alkyl-substituted phenyl, phenoxy orphenylthio.

[0358] R⁶ and R⁷ independently of one another each very particularlypreferably represent hydrogen, represent C₁-C₄-alkyl, C₃-C₆-cycloalkyl,C₁-C₄-alkoxy, C₃-C₄-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, representoptionally fluorine-, chlorine-, bromine-, trifluoromethyl-, methyl- ormethoxy-substituted phenyl, represent optionally fluorine-, chlorine-,bromine-, methyl-, trifluoromethyl- or methoxy-substituted benzyl, ortogether represent a C₅-C₆-alkylene radical in which optionally onemethylene group is replaced by oxygen or sulphur.

[0359] The abovementioned general or preferred radical definitions orillustrations can be combined with each other as desired, i.e. includingcombinations between the respective ranges and preferred ranges. Theyapply both to the end products and, correspondingly, to the precursorsand intermediates.

[0360] Preference according to the invention is given to the compoundsof the formula (I) which contain a combination of the meanings listedabove as being preferred (preferable).

[0361] Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

[0362] Very particular preference according to the invention is given tothe compounds of the formula (I) which contain a combination of themeanings listed above as being very particularly preferred.

[0363] Compounds of the formula (I) in which G represents hydrogen areparticularly preferred.

[0364] Saturated or unsaturated hydrocarbon radicals such as alkyl oralkenyl may in each case be straight-chain or branched as far as this ispossible, including in combination with heteroatoms, such as, forexample, in alkoxy.

[0365] Unless stated otherwise, optionally substituted radicals may bemono- or polysubstituted, and in the case of polysubstitutions thesubstituents may be identical or different.

[0366] Besides the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-1-a) may be specificallymentioned:

TABLE 1 X = CH₃, Z = CH₃, V¹ = H, V² = H. A B D CH₃ H H C₂H₅ H H C₃H₇ HH i-C₃H₇ H H C₄H₉ H H i-C₄H₉ H H s-C₄H₉ H H t-C₄H₉ H H CH₃ CH₃ H C₂H₅CH₃ H C₃H₇ CH₃ H i-C₃H₇ CH₃ H C₄H₉ CH₃ H i-C₄H₉ CH₃ H s-C₄H₉ CH₃ Ht-C₄H₉ CH₃ H C₂H₅ C₂H₅ H C₃H₇ C₃H₇ H

CH₃ H

CH₃ H

CH₃ H —(CH₂)₂— H —(CH₂)₄— H —(CH₂)₅— H —(CH₂)₆— H —(CH₂)₇— H—(CH₂)₂—O—(CH₂)₂— H —CH₂—O—(CH₂)₃— H —(CH₂)₂—S—(CH₂)₂— H—CH₂—CHCH₃—(CH₂)₃— H —(CH₂)₂—CHCH₃—(CH₂)₂— H —(CH₂)₂—CHC₂H₅—(CH₂)₂— H—(CH₂)₂—CHC₃H₇—(CH₂)₂— H —(CH₂)₂—CHi-C₃H₇—(CH₂)₂— H—(CH₂)₂—CHOCH₃—(CH₂)₂— H —(CH₂)₂—CHOC₂H₅—(CH₂)₂— H—(CH₂)₂—CHOC₃H₇—(CH₂)₂— H —(CH₂)₂—CHi-C₃H₇—(CH₂)₂— H—CH₂)₂—C(CH₃)₂—(CH₂)₂— H —CH₂—(CHCH₃)₂—(CH₂)₂— H

H

H

H

H

H A D B —(CH₂)₃— H —(CH₂)₄— H —CH₂—CHCH₃—CH₂— H —CH₂—CH₂—CHCH₃— H—CH₂—CHCH₃—CHCH₃— H —CH₂—S—CH₂— H —CH₂—S—(CH₂)₂— H —(CH₂)₂—S—CH₂— H

H H CH₃ H H C₂H₅ H H C₃H₇ H H i-C₃H₇ H H

H H

H H

H CH₃ CH₃ H CH₃ C₂H₅ H CH₃ C₃H₇ H CH₃ i-C₃H₇ H CH₃

H CH₃

H CH₃

H C₂H₅ CH₃ H C₂H₅ C₂H₅ H

[0367] Table 2: A, B and D are each as given in Table 1

[0368] X=C₂H₅; Z=CH₃; V¹=H; V²=H.

[0369] Table 3: A, B and D are each as given in Table 1

[0370] X=C₂H₅; Z=C₂H₅; V¹=H; V²=H.

[0371] Table 4: A, B and D are each as given in Table 1

[0372] X=CH₃; Z=CH₃; V¹=4-Cl; V²=H.

[0373] Table 5: A, B and D are each as given in Table 1

[0374] X C₂H₅; Z=CH₃; V¹=4Cl; V²H.

[0375] Table 6: A, B and D are each as given in Table 1

[0376] X=C₂H₅; Z=C₂H₅; V¹=4-Cl; V²=H.

[0377] Table 7: A, B and D are each as given in Table 1

[0378] X=CH₃; Z=CH₃; V¹=3-Cl; V²=H.

[0379] Table 8: A, B and D are each as given in Table 1

[0380] X=C₂H₅; Z=CH₃; V¹=3-Cl; V²=H.

[0381] Table 9: A, B and D are each as given in Table 1

[0382] X=C₂H₅; Z=C₂H₅; V¹=3-Cl; V²=H.

[0383] Table 10: A, B and D are each as given in Table 1

[0384] X=CH₃; Z=CH₃; V¹=2-Cl; V²=4-Cl.

[0385] p Table 11: A, B and D are each as given in Table 1

[0386] X=C₂H₅; Z=CH₃; V¹=2-Cl; V²=4-Cl.

[0387] Table 12: A, B and D are each as given in Table 1

[0388] X=C₂H₅; Z=C₂H₅; V¹=2-Cl; V²=4-Cl.

[0389] Table 13: A, B and D are each as given in Table 1

[0390] X=CH₃; Z=CH₃; V¹=4-CF₃; V²=H.

[0391] Table 14: A, B and D are each as given in Table 1

[0392] X=C₂H₅; Z=CH₃; V¹=4-CF₃; V²=H.

[0393] Table 15: A, B and D are each as given in Table 1

[0394] X=C₂H₅; Z=C₂H₅; V¹=4-CF₃; V²=H.

[0395] Table 16: A, B and D are each as given in Table 1

[0396] X=CH₃; Z=CH₃; V¹=4-CH₃; V²H.

[0397] Table 17: A, B and D are each as given in Table 1

[0398] X=C₂H₅; Z=CH₃; V¹=4-CH₃; V2=H.

[0399] Table 18: A, B and D are each as given in Table 1

[0400] X=C₂H₅; Z=C₂H₅; V¹=4-CH₃; V2=H.

[0401] Table 19: A, B and D are each as given in Table 1

[0402] X=CH₃; Z=CH₃; V¹=4-OCH₃; V²=H.

[0403] Table 20: A, B and D are each as given in Table 1

[0404] X=C₂H₅; Z=CH₃; V¹=4-OCH₃; V²=H.

[0405] Table 21: A, B and D are each as given in Table 1

[0406] X=C₂H₅; Z=C₂H₅; V¹=4-OCH₃; V²=H.

[0407] Besides the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-2-a) may be specificallymentioned: TABLE 22 X = CH₃, Z = CH₃, V¹ = H, V² = H.

A B CH₃ H C₂H₅ H C₃H₇ H i-C₃H₇ H C₄H₉ H i-C₄H₉ H s-C₄H₉ H t-C₄H₉ H CH₃CH₃ C₂H₅ CH₃ C₃H₇ CH₃ i-C₃H₇ CH₃ C₄H₉ CH₃ i-C₄H₉ CH₃ s-C₄H₉ CH₃ t-C₄H₉CH₃ C₂H₅ C₂H₅ C₃H₇ C₃H₇

CH₃

CH₃

CH₃ —(CH₂)₂— —(CH₂)₄— —(CH₂)₅— —(CH₂)₆— —(CH₂)₇— —(CH₂)₂—O—(CH₂)₂——CH₂—O—(CH₂)₃— —(CH₂)₂—S—(CH₂)₂— —CH₂—CHCH₃—(CH₂)₃——(CH₂)₂—CHCH₃—(CH₂)₂— (CH₂)₂—CHC₂H₅—(CH₂)₂— —(CH₂)₂—CHC₃H₇—(CH₂)₂——(CH₂)₂—CHi-C₃H₇—(CH₂)₂— —(CH₂)₂—CHOCH₃—(CH₂)₂— —(CH₂)₂—CHOC₂H₅—(CH₂)₂——(CH₂)₂—CHOC₃H₇—(CH₂)₂— —(CH₂)₂—CHi-C₃H₇—(CH₂)₂— —(CH₂)₂—C(CH₃)₂—(CH₂)₂——CH₂—(CHCH₃)₂—(CH₂)₂—

[0408] Table 23: A and B are each as given in Table 22

[0409] X=C₂H₅; Z=CH₃; V¹=H; V²=H.

[0410] Table 24: A and B are each as given in Table 22

[0411] X=C₂H₅; Z=C₂H₅; V¹=H; V²=H.

[0412] Table 25: A and B are each as given in Table 22

[0413] X=CH₃; Z=CH₃; V¹=4-Cl; V²=H.

[0414] Table 26: A and B are each as given in Table 22

[0415] X=C₂H₅; Z=CH₃; V¹=4-Cl; V²=H.

[0416] Table 27: A and B are each as given in Table 22

[0417] X=C₂H₅; Z=C₂H₅; V¹=4-Cl; V²=H.

[0418] Table 28: A and B are each as given in Table 22

[0419] X=CH₃; Z=CH₃; V¹=3-Cl; V²=H.

[0420] Table 29: A and B are each as given in Table 22

[0421] X=C₂H₅; Z=CH₃; V¹=3-Cl; V²=H.

[0422] Table 30: A and B are each as given in Table 22

[0423] X=C₂H₅; Z=C₂H₅; V¹3-Cl; V² H.

[0424] Table 31: A and B are each as given in Table 22

[0425] X=CH₃; Z=CH₃; V¹4-CF₃; V²=H.

[0426] Table 32: A and B are each as given in Table 22

[0427] X=C₂H₅; Z=CH₃; V¹4-CF₃; V²=H

[0428] Table 33: A and B are each as given in Table 22

[0429] X=C₂H₅; Z=C₂H₅; V¹=4-CF₃; V²=H.

[0430] Table 34: A and B are each as given in Table 22

[0431] X=CH₃; Z=CH₃; V¹=2-Cl; V²32 4-Cl.

[0432] Table 35: A and B are each as given in Table 22

[0433] X=C₂H₅; Z=CH₃; V¹=2-Cl; V²=4-Cl.

[0434] Table 36: A and B are each as given in Table 22

[0435] X=C₂H₅; Z=C₂H₅; V¹=2-CF; V¹=4-Cl.

[0436] Table 37: A and B are each as given in Table 22

[0437] X=CH₃; Z=CH₃; V1=4-CH₃; V²=H.

[0438] Table 38: A and B are each as given in Table 22

[0439] X=C₂H₅; Z=CH₃; V¹=4-CH₃; V²=H.

[0440] Table 39: A and B are each as given in Table 22

[0441] X=C₂H₅; Z=C₂H₅; V¹=4-CH₃; V²=H.

[0442] Table 40: A and B are each as given in Table 22

[0443] X=CH₃ Z=CH₃; V¹=4-OCH₃; V2=H.

[0444] Table 41: A and B are each as given in Table 22

[0445] X=C₂H₅; Z=CH₃; V¹=4-OCH₃; V²=H.

[0446] Table 42: A and B are each as given in Table 22

[0447] X=C₂H₅; Z=C₂H₅; =4-OCH₃; V²=H.

[0448] Using, in accordance with process (A), ethylN-[(2-methyl-4-phenyl)-phenylacetyl]-1-amino-cyclohexane-carboxylate asstarting material, the course of the process according to the inventioncan be represented by the following equation:

[0449] Using, in accordance with process (B), ethyl (B)O-[(2-chloro-4-(4-chloro)-phenyl)-phenylacetyl]-2-hydroxyisobutyrate,the course of the process according to the invention can be representedby the following equation:

[0450] Using, in accordance with process (C), ethyl2-[(2,6-dimethyl4-phenyl)-phenyl]-4-(4-methoxy)-benzylmercapto4-methyl-3-oxo-valerate,the course of the process according to the invention can be representedby the following equation:

[0451] Using, for example in accordance with process (D-α),chlorocarbonyl 3-[(2-chloro-6-methyl-4-(4-methyl)-phenyl)-phenyl] keteneand 1,2-diazacyclopentane as starting materials, the course of theprocess according to the invention can be represented by the followingequation:

[0452] Using, for example in accordance with process (D-β), diethyl3-[2-methyl-4-(3-chloro-phenyl)]-phenylmalonate and1,2-diazacyclopentane as starting materials, the course of the processaccording to the invention can be represented by the following equation:

[0453] Using, for example in accordance with process (E), chlorocarbonyl2-[(2-ethyl-6-methyl-(4-trifluoromethoxy-phenyl))-phenyl] ketene andacetone as starting materials, the course of the process according tothe invention can be represented by the following equation:

[0454] Using, for example in accordance with process (F), chlorocarbonyl2-[(2,6-dimethyl-4-phenyl)-phenyl] ketene and thiobenzamide as startingmaterials, the course of the process according to the invention can berepresented by the following equation:

[0455] Using, in accordance with process (G), ethyl5-[(2-chloro-6-methyl4-phenyl)-phenyl]-2,3-tetramethylene-4-oxo-valerate,the course of the process according to the invention can be representedby the following equation:

[0456] Using, in accordance with process (H), ethyl5-[(2,6-dichloro-4-phenyl)-phenyl]-2,2-dimethyl-5-oxo-hexanoate, thecourse of the process according to the invention can be represented bythe following equation:

[0457] Using, in accordance with process (I),3-[(2,6-dimethyl-4-bromo)-phenyl]-4,4-(pentamethylene)-pyrrolidine-2,4-dioneand 4-chlorophenylboronic acid as starting materials, the course of thereaction can be represented by the following scheme:

[0458] Using, in accordance with process (Jα),3-[(2-chloro-4-(3-chloro-phenyl))-phenyl]-5,5-dimethylpyrrolidine-2,4-dioneand pivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the following equation:

[0459] Using, in accordance with process (J), (variant β),3-[(2-ethyl-4-(4-methoxyphenyl))-phenyl]-4-hydroxy-5-phenyl-Δ³-dihydrofuran-2-oneand acetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the following equation:

[0460] Using, in accordance with process (K),8-[(2,6-diethyl-4-phenyl)-phenyl]-1,6-diazahbicyclo-(4.30^(1.6))-nonane-7,9-dioneand ethoxyethyl chloroformate as starting materials, the course of theprocess according to the invention can be represented by the followingequation:

[0461] Using, in accordance with process (L),3-[(2-chloro-4-(4-fluoro-phenyl))-phenyl]-4-hydroxy-5-methyl-6-(3-pyridyl)-pyroneand methyl chloromonothioformate as starting materials, the course ofthe reaction can be represented as follows:

[0462] Using, in accordance with process (M),2-[(2,6-dimethyl4-(4-methyl-phenyl))-phenyl]-5,5-pentamethylene-pyrrolidine-2,4-dioneand methanesulphonyl chloride as starting materials, the course of thereaction can be represented by the following equation:

[0463] Using, in accordance with process (N),2-[(2-methyl4-phenyl)-phenyl]-4-hydroxy-5,5-dimethyl-Δ³-dihydrofuran-2-oneand 2,2,2-trifluoroethyl methanethiophosphonyl chloride as startingmaterials, the course of the reaction can be represented by thefollowing equation:

[0464] Using, in accordance with process (O),3-[(2-trifluoromethyl-4-(4-trifluoromethylphenyl))-phenyl]-5-cyclopropyl-5-methyl-pyrrolidine-2,4-dioneand NaOH as components, the course of the process according to theinvention can be represented by the following equation:

[0465] Using, in accordance with process (P), variant α,3-[(2-methyl-4-(3-trifluoromethylphenyl))-phenyl]4-hydroxy-5-tetramethylene-Δ³-dihydro-furan-2-oneand ethyl isocyanate as starting materials, the course of the reactioncan be represented by the following equation:

[0466] Using, in accordance with process (P), variant β,3-[(2-chloro-4-phenyl)-phenyl]-5-methyl-pyrrolidine-2,4-dione anddimethylcarbamoyl chloride as starting materials, the course of thereaction can be represented by the following scheme:

[0467] The compounds of the formula (II)

[0468] in which

[0469] A, B, D, X, Y, Z and R⁸ are each as defined above

[0470] which are required as starting materials in the process (a)according to the invention are novel.

[0471] The acylamino acid esters of the formula (II) are obtained, forexample, when amino acid derivatives of the formula (XXIII)

[0472] in which

[0473] A, B, R⁸ and D are each as defined above

[0474] are acylated with substituted phenylacetyl halides of the formula(XXIV)

[0475] in which

[0476] X, Y and Z are each as defined above and

[0477] Hal represents chlorine or bromine

[0478] (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem.6, 341-5, 1968)

[0479] or when acylamino acids of the formula (XXV)

[0480] in which

[0481] A, B, D, X, Y and Z are each as defined above

[0482] are esterified (Chem. Ind. (London) 1568 (1968)).

[0483] The compounds of the formula (XXV)

[0484] in which

[0485] A, B, D, X, Y and Z are each as defined above

[0486] are novel.

[0487] The compounds of the formula (XXV) are obtained when amino acidsof the formula (XXVI)

[0488] in which

[0489] A, B and D are each as defined above

[0490] are acylated with substituted phenylacetyl halides of the formula(XXIV)

[0491] in which

[0492] X, Y and Z are each as defined above and

[0493] Hal represents chlorine or bromine,

[0494] for example according to Schotten-Baumann (Organikum, VEBDeutscher Verlag der Wissenschaften, Berlin 1977, p. 505).

[0495] The compounds of the formula (XXIV) are novel. They can beprepared by processes which are known in principle (see, for example, H.Henecka, Houben-Weyl, Methoden der Organischen Chemie, Vol. 8, p.467-469 (1952)).

[0496] The compounds of the formula (XXIV) are obtained, for example, byreacting substituted phenylacetic acids of the formula (XXVII)

[0497] in which

[0498] X, Y and Z are each as defined above

[0499] with halogenating agents (for example thionyl chloride, thionylbromide, oxalyl chloride, phosgene, phosphorus trichloride, phosphorustribromide or phosphorus pentachloride), if appropriate in the presenceof a diluent (for example optionally chlorinated aliphatic or aromatichydrocarbons such as toluene or methylene chloride), at temperaturesfrom −20° C. to 150° C., preferably from −10° C. to 100° C.

[0500] Some of the compounds of the formulae (XXII) and (XXVI) areknown, and/or they can be prepared by known processes (see, for example,Compagnon, Miocque Ann. Chim. (Paris) [14] 5, p. 11-22,23-27 (1970)).

[0501] The substituted cyclic aminocarboxylic acids of the formula(XXVIa) in which A and B form a ring are generally obtainable by theBucherer-Bergs synthesis or by the Strecker synthesis and are in eachcase obtained in different isomer forms. Thus, under the conditions ofthe Bucherer-Bergs synthesis, the isomers (for simplicity called βbelow), in which the radicals R and the carboxyl group are equatorialare predominantly obtained, while under the conditions of the Streckersynthesis the isomers (for simplicity called a below) in which the aminogroup and the radicals R are equatorial are predominantly obtained.

[0502] (L. Munday, J. Chem. Soc. 4372 (1961); J. T. Eward, C.Jitrangeri, Can. J. Chem. 53 3339 (1975)

[0503] Furthermore, the starting materials of the formula (II)

[0504] in which

[0505] A, B, D, X, Y, Z and R⁸ are each as defined above

[0506] used in the above process (A) can be prepared when aminonitrilesof the formula (XXXVIII)

[0507] in which

[0508] A, B and D are each as defined above

[0509] are reacted with substituted phenylacetyl halides of the formula(XXIV)

[0510] in which

[0511] X, Y, Z and Hal are each as defined above

[0512] to give compounds of the formula (XXIX)

[0513] in which

[0514] A, B, D, X, Y and Z are each as defined above

[0515] and these are subsequently subjected to acidic alcoholysis.

[0516] The compounds of the formula (XXIX) are likewise novel

[0517] The compounds of the formula (III)

[0518] in which

[0519] A, B, X, Y, Z and R⁸ are each as defined above

[0520] required as starting materials in the process (B) according tothe invention are novel.

[0521] They can be prepared by methods known in principle.

[0522] Thus, the compounds of the formula (III), for example, areobtained when

[0523] 2-hydroxycarboxylic esters of the formula (XXX)

[0524] in which

[0525] A, B and R⁸ are each as defined above

[0526] are acylated with substituted phenylacetyl halides of the formula(XXIV)

[0527] in which

[0528] X, Y, Z and Hal are each as defined above

[0529] (Chem. Reviews 52, 237-416 (1953)).

[0530] Furthermore, compounds of the formula (III) are obtained when

[0531] substituted phenylacetic acids of the formula (XXVII)

[0532] in which

[0533] X, Y and Z are each as defined above

[0534] are alkylated with a-halogenocarboxylic esters of the formula(XXXI)

[0535] in which

[0536] A, B and R⁸ are each as defined above and

[0537] Hal represents chlorine or bromine.

[0538] The compounds of the formula (XXVII) are novel.

[0539] The compounds of the formula (XXXI) are known and in most casescommercially available.

[0540] The compounds of the formula (XXVII)

[0541] in which

[0542] X, Y and Z are each as defined above

[0543] are obtained, for example,

[0544] α) when compounds of the formula (XXVII-a)

[0545]  in which

[0546] X and Z are each as defined above

[0547] Y′ represents chlorine or bromine, preferably represents bromine,

[0548] are reacted with boronic acids of the formula (XII)

[0549]  in which

[0550] Y is as defined above

[0551] in the presence of a solvent, a base and a catalyst (preferably apalladium complex, such as, for example, tetrakis(triphenylphosphine)-palladium or

[0552] β) when phenylacetic esters of the formula (XXXII)

[0553]  in which

[0554] X, Y, Z and R⁸ are each as defined above

[0555] are hydrolysed under generally known standard conditions in thepresence of acids or bases, in the presence of a solvent, or

[0556] γ) when phenylacetic acids of the formula (XVII-b)

[0557]  in which

[0558] X and Z are each as defined above

[0559] are reacted with halogen compounds of the formula (XXXIII),

Y-Hal  (XXXIII)

[0560]  in which

[0561] Y is as defined above and

[0562] Hal represents chlorine, bromine or iodine

[0563] in the presence of a solvent, a base and a catalyst (preferablyone of the abovementioned palladium complexes).

[0564] The compounds of the formulae (XII) and (XXXIII) are known, someof them are commercially available, or they can be prepared by processesknown in principle. Some of the phenylacetic acids of the formula(XXVII-a) are known from WO 96/35 664 and WO 97/02243, or they can beprepared by the processes described therein.

[0565] The compounds of the formula (XXVII-b) and (XXXII) are novel.

[0566] The compounds of the formula (XXVII-b)

[0567] in which

[0568] X and Z are each as defined above

[0569] are obtained, for example, when phenylacetic acids of the formula(XXVII-a)

[0570] in which

[0571] X, Y′ and Z are each as defined above

[0572] are reacted with lithium compounds of the formula (XXXIV)

Li—R²¹  (XXXIV)

[0573] in which

[0574] R²¹ represents C₁-C₈-alkyl or phenyl, preferably representsn-C₄H₉,

[0575] and boronic esters of the formula (XXXV)

B(OR⁸)₃  (XXXV)

[0576] in which

[0577] R⁸ is as defined above

[0578] in the presence of a diluent.

[0579] The compounds of the formulae (XXXIV) and (XXXV) are commerciallyavailable compounds.

[0580] The compounds of the formula (XXXII)

[0581] in which

[0582] X, Y, Z and R⁸ are each as defined above

[0583] are obtained, for example,

[0584] when phenylacetic esters of the formula (XXII-a)

[0585] in which

[0586] R⁸, X, Y′ and Z are each as defined above

[0587] are reacted with boronic acids of the formula (XII)

[0588] in which

[0589] Y is as defined above

[0590] in the presence of a solvent, a base and a catalyst (preferablyone of the abovementioned palladium complexes).

[0591] Some of the phenylacetic esters of the formula (XXXII-a) areknown from the applications WO 96/35 664 and WO 97/02 243, or they canbe prepared by the processes described therein.

[0592] The compounds of the formula (IV)

[0593] in which

[0594] A, B, W, X, Y, Z and R⁸ are each as defined above

[0595] required as starting materials in the above process (C) arenovel.

[0596] They can be prepared by methods known in principle.

[0597] The compounds of the formula (IV) are obtained, for example, whensubstituted phenylacetic esters of the formula (XXXII)

[0598] in which

[0599] X, Y, R⁸ and Z are each as defined above

[0600] are acylated with 2-benzylthio-carbonyl halides of the formula(XXXVI)

[0601] in which

[0602] A, B and W are each as defined above and

[0603] Hal represents halogen (in particular chlorine or bromine)

[0604] in the presence of strong bases (see, for example, M. S.Chambers, E. J. Thomas, D. J. Williams, J. Chem. Soc. Chem. Commun.,(1987), 1228).

[0605] The compounds of the formula (XXXII) are novel. Compounds of theformula (XXII) are obtained, for example, when compounds of the formula(XXII)

[0606] in which

[0607] X, Y and Z are each as defined above

[0608] are esterified in the presence of alcohols and dehydrating agents(for example conc. sulphuric acid),

[0609] or when alcohols are acylated with compounds of the formula(XXIV)

[0610] in which

[0611] X, Y, Z and Hal are each as defined above

[0612] (Chem. Reviews 52 237-416 (1953)).

[0613] Some of the benzylthio-carbonyl halides of the formula (XXXVI)are known, and/or they can be prepared by known processes (J.Antibiotics (1983), 26, 1589).

[0614] The halogenocarbonyl ketenes of the formula (V) required asstarting materials in the above processes (D), (E) and (F) are novel.They can be prepared by methods which are generally known in principle(cf., for example, Org. Prep. Proced. Int., 7, (4), 155-158, 1975 and DE1 945 703). Thus, for example, the compounds of the formula (V)

[0615] in which

[0616] X, Y and Z are each as defined above and

[0617] Hal represents chlorine or bromine

[0618] are obtained when

[0619] substituted phenylmalonic acids of the formula (XXXVII)

[0620] in which

[0621] X, Y and Z are each as defined above

[0622] are reacted with acyl halides, such as, for example, thionylchloride, phosphorus(V) chloride, phosphorus(III) chloride, oxalylchloride, phosgene or thionyl bromide, if appropriate in the presence ofcatalysts, such as, for example, dimethylformamide,methyl-steryl-formamide or triphenylphosphine and if appropriate in thepresence of bases such as, for example, pyridine or triethylamine.

[0623] The substituted phenylmalonic acids of the formula (XXXVII) arenovel. They can be prepared by generally known processes (cf., forexample, Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin1977, p. 517 ff, EP-A-528 156, WO 96/35 664, WO 97/02 243).

[0624] Thus, phenylmalonic acids of the formula (XXXVII)

[0625] in which

[0626] X, Y and Z are each as defined above

[0627] are obtained when phenylmalonic esters of the formula (VI)

[0628] in which

[0629] X, Y, Z and R⁸ are each as defined above

[0630] are initially hydrolysed in the presence of a base and in asolvent and subsequently carefully acidified (EP-528 156, WO 96/35 664,WO 97/02 243).

[0631] The malonic esters of the formula (VI)

[0632] in which

[0633] X, Y, Z and R⁸ are each as defined above

[0634] are novel.

[0635] They can be prepared by generally known methods of organicchemistry (cf., for example, Tetrahedron Lett. 27, 2763 (1986) andOrganikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, p. 587ff.). Some of the hydrazines of the formula (VII)

A-NH—NH-D  (VII),

[0636] in which

[0637] A and D are each as defined above

[0638] required as starting materials for the process (D) according tothe invention are known, and/or they can be prepared by methods knownfrom the literature (cf., for example, Liebigs Ann. Chem. 585, 6 (1954);Reaktionen der organischen Synthese, C. Ferri, p. 212, 513; Georg ThiemeVerlag Stuttgart, 1978; Liebigs Ann. Chem. 443, 242 (1925); Chem. Ber.98, 2551 (1965), EP-508 126).

[0639] The carbonyl compounds of the formula (VIII)

[0640] in which

[0641] A and D are each as defined above

[0642] or their silyl enol ethers of the formula (VIIIa)

[0643] in which

[0644] A, D and R⁸ are each as defined above

[0645] required as starting materials for the process (E) according tothe invention are commercially available, generally known compounds orcompounds which are obtainable by known processes.

[0646] The preparation of the ketene acid chlorides of the formula (V),required as starting materials for carrying out the process (F)according to the invention has already been described above. Thethioamides of the formula (IX)

[0647] in which

[0648] A is as defined above

[0649] required for carrying out the process (F) according to theinvention are compounds which are generally known in organic chemistry.

[0650] The compounds of the formula (X)

[0651] in which

[0652] A, B, Q ¹, Q², X, Y, Z and R⁸ are each as defined above

[0653] required as starting materials in the above process (G) arenovel.

[0654] They can be prepared by methods known in principle.

[0655] The 5-aryl-4-ketocarboxylic esters of the formula (X) areobtained, for example, when 5-aryl-4-ketocarboxylic acids of the formula(XXXVIII)

[0656] in which

[0657] X, Y, Z, A, B, Q¹ and Q² are each as defined above

[0658] are esterified (cf., for example, Organikum, 15th edition,Berlin, 1977, page 499) or alkylated (see Preparation Example).

[0659] The 5-aryl-4-ketocarboxylic acids of the formula (XXXVIII)

[0660] in which

[0661] A, B, Q¹, Q², X, Y and Z are each as defined above are novel butcan be prepared by methods known in principle (see Preparation Example).

[0662] The 5-aryl4-ketocarboxylic acids of the formula (XXXVIII) areobtained, for example, when 2-phenyl-3-oxo-adipic esters of the formula(XXXIX)

[0663] in which

[0664] A, B, D¹, D², X, Y and Z are each as defined above and

[0665] R⁸ and R⁸′ each represent alkyl (in particular C₁-C₈-alkyl)

[0666] are decarboxylated, if appropriate in the presence of a diluentand if appropriate in the presence of a base or acid (cf., for example,Organikum, 15th edition, Berlin, 1977, pages 519 to 521).

[0667] The compounds of the formula (XXXIX)

[0668] in which

[0669] A, B, Q¹, Q², X, Y, Z, R⁸, R⁸′ are each as defined above

[0670] are novel.

[0671] The compounds of the formula LXIX) are obtained, for example,

[0672] when dicarboxylic monoester chlorides of the formula (XL),

[0673] in which

[0674] A, B, Q¹, Q² and R⁸ are each as defined above and

[0675] Hal represents chlorine or bromine

[0676] or carboxylic anhydrides of the formula (XLI)

[0677] in which

[0678] A, B, Q¹ and Q² are each as defined above

[0679] are acylated with a phenyl acetic ester of the formula (XXII)

[0680] in which

[0681] X, Y, Z and R⁸′ are each as defined above

[0682] in the presence of a diluent and in the presence of a base (cf.,for example, M. S. Chambers, E. J. Thomas, D. J. Williams, J. Chem. Soc.Chem. Commun., (1987), 1228, cf. also the Preparation Examples).

[0683] Some of the compounds of the formulae (XL) and (XLI) are knowncompounds of organic chemistry, and/or they can be prepared in a simplemanner by methods known in principle.

[0684] The compounds of the formula (XI)

[0685] in which

[0686] A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y, Z and R⁸ are each as defined above

[0687] required as starting materials in the above process (H) arenovel.

[0688] They can be prepared by methods known in principle.

[0689] The 6-aryl-5-ketocarboxylic esters of the formula (XI) areobtained, for example, when 6-aryl-5-ketocarboxylic acids of the formula(XLII)

[0690] in which

[0691] A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above

[0692] are esterified (cf., for example, Organikum, 15th edition,Berlin, 1977, page 499 and Preparation Example).

[0693] The 6-aryl-5-ketocarboxylic acids of the formula (XLII)

[0694] in which

[0695] A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above

[0696] are novel. They can be prepared by methods known in principle,for example by hydrolysing and decarboxylating

[0697] substituted 2-phenyl-3-oxo-heptanedioic esters of the formula(XLIII)

[0698] in which

[0699] A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above and

[0700] R⁸ and R⁸′ are each alkyl (preferably C₁-C₆-alkyl),

[0701] if appropriate in the presence of a diluent and if appropriate inthe presence of a base or acid (cf., for example, Organikum, 15thedition, Berlin, 1977, page 519 to 521 and Preparation Example).

[0702] The compounds of the formula (XLIII)

[0703] in which

[0704] A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y, Z, R⁸ and R⁸′ are each as definedabove

[0705] are novel. They can be obtained

[0706] when dicarboxylic anhydrides of the formula (XLIV),

[0707] in which

[0708] A, B, Q³, Q⁴, Q⁵ and Q⁶ are each as defined above are condensedwith a substituted phenylacetic ester of the formula (XII)

[0709] in which

[0710] X, Y, Z and R⁸′ are each as defined above

[0711] in the presence of a diluent and in the presence of a base.

[0712] Some of the compounds of the formula (XLIV) are known, and/orthey can be prepared by known processes.

[0713] The compounds of the formula (XXXII) have already been describedunder the precursors for the process (B). Furthermore, compounds of theformula (XXXII) are obtained by reacting substituted1,1,1-trichloro-2-phenylethanes of the formula (XLV)

[0714] in which

[0715] X, Y and Z are each as defined above

[0716] initially with alkoxides (for example alkali metal alkoxides suchas sodium methoxide or sodium ethoxide) in the presence of a diluent(for example the alcohol derived from the alkoxide) at temperaturesbetween 0° C. and 150° C., preferably between 20° C. and 120° C., andsubsequently with an acid (preferably an inorganic acid such as, forexample, sulphuric acid) at temperatures between −20° C. and 150° C.,preferably between 0C and 100° C. (cf. DE 3 314 249).

[0717] The compounds of the formula (XLV) are novel, they can beprepared by processes known in principle.

[0718] The compounds of the formula (XLV) are obtained, for example,when anilines of the formula (XLVI)

[0719] in which

[0720] X, Y and Z are each as defined above

[0721] are reacted with vinylidene chloride (CH₂═CCl₂) in the presenceof an alkyl nitrite of the formula (XLVII)

R²¹—ONO  (XLVII)

[0722] in which

[0723] R²¹ represents alkyl, preferably C₁-C₆-alkyl,

[0724] in the presence of copper(II) chloride and, if appropriate, inthe presence of a diluent (for example an aliphatic nitrile such asacetonitrile), at a temperature of from −20° C. to 80° C., preferablyfrom 0° C. to 60° C.

[0725] The compounds of the formula (XLVII) are known compounds oforganic chemistry. Copper(II) chloride and vinylidene chloride have beenknown for a long time and are commercially available.

[0726] The compounds of the formula (XLVI) are novel.

[0727] Compounds of the formula (XLVI)

[0728] in which

[0729] X, Y and Z are each as defined above,

[0730] for example, are obtained when anilines of the formula (XLVI-a)

[0731] in which

[0732] X and Z are each as defined above

[0733] Y′ represents halogen (preferably represents bromine) are reactedwith boronic acids of the formula (XII)

[0734] in which

[0735] Y is as defined above

[0736] in the presence of a solvent, a base and a catalyst (preferably apalladium complex, such as, for example, tetrakis(tripheylphosphine)palladium.

[0737] Some of the compounds of the formulae (I-1′-a) to (I-8′-a) inwhich A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X and Z are each as defined aboveand Y′ represents chlorine and bromine, preferably represents bromine,and which are required as starting materials in the above process (I)are known (WO 96/35 664, WO 97/02 243) or they can be prepared by theprocesses described therein or by processes (A) to (H).

[0738] Some of the boronic acids of the formula (XII)

[0739] in which

[0740] Y is as defined above

[0741] are commercially available, or they can be prepared in a simplemanner by generally known processes.

[0742] The acyl halides of the formula (XIII), carboxylic anhydrides ofthe formula (XIV), chloroformic esters or chloroformic thioesters of theformula (XV), chloromonothioformic esters or chlorodithioformic estersof the formula (XVI), sulphonyl chlorides of the formula (XVII),phosphorus compounds of the formula (XVIII) and metal hydroxides, metalalkoxides or amines of the formulae (XIX) and (XX) and isocyanates ofthe formula (XXI) and carbamoyl chlorides of the formula (XXII)furthermore required as starting materials for carrying out theprocesses (J), (K), (L), (M), (N), (O) and (P) according to theinvention are generally known compounds of organic or inorganicchemistry.

[0743] Moreover, the compounds of the formulae (VII), (VIII), (IX),(XIII) to (XXIII), (XXVI), (XXVIII), (XXX), (XXXVI), (XL), (XLI) and(XLVI-a) are known from the patent applications cited at the outset,and/or they can be prepared by the methods given therein.

[0744] The process (A) is characterized in that compounds of the formula(II) in which A, B, D, X, Y, Z and R⁸ are each as defined above aresubjected to an intramolecular condensation in the presence of a base.

[0745] Suitable diluents for the process (A) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone, andalso alcohols, such as methanol, ethanol, propanol, iso-propanol,butanol, iso-butanol and tert-butanol.

[0746] Suitable bases (deprotonating agents) for carrying out theprocess (A) according to the invention are all customary protonacceptors. Preference is given to using alkali metal and alkaline earthmetal oxides, hydroxides and carbonates, such as sodium hydroxide,potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate,potassium carbonate and calcium carbonate, which can also be employed inthe presence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-CIO)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium andpotassium can also be used. Furthermore, alkali metal and alkaline earthmetal amides and hydrides, such as sodium amide, sodium hydride andcalcium hydride, and additionally also alkali metal alkoxides, such assodium methoxide, sodium ethoxide and potassium tert-butoxide can beemployed.

[0747] When carrying out the process (A) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

[0748] The process (A) according to the invention is generally carriedout under atmospheric pressure.

[0749] When carrying out process (A) according to the invention, thereaction components of the formula (II) and the deprotonating bases aregenerally employed in approximately double-equimolar amounts. However,it is also possible to use a larger excess (up to 3 mol) of onecomponent or the other.

[0750] The process (B) is characterized in that compounds of the formula(III) in which A, B, X, Y, Z and R⁸ are each as defined above aresubjected to an intramolecular condensation in the presence of a diluentand in the presence of a base.

[0751] Suitable diluents for the process (B) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone, andalso alcohols, such as methanol, ethanol, propanol, iso-propanol,butanol, iso-butanol and tert-butanol.

[0752] Suitable bases (deprotonating agents) for carrying out theprocess (B) according to the invention are all customary protonacceptors. Preference is given to using alkali metal and alkaline earthmetal oxides, hydroxides and carbonates, such as sodium hydroxide,potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate,potassium carbonate and calcium carbonate, which can also be employed inthe presence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium andpotassium can also be used. Furthermore, alkali metal and alkaline earthmetal amides and hydrides, such as sodium amide, sodium hydride andcalcium hydride, and additionally also alkali metal alkoxides, such assodium methoxide, sodium ethoxide and potassium tert-butoxide can beemployed.

[0753] When carrying out the process (B) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

[0754] The process (B) according to the invention is generally carriedout under atmospheric pressure.

[0755] When carrying out the process (B) according to the invention, thereaction components of the formula (III) and the deprotonating bases aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

[0756] The process (C) is characterized in that compounds of the formula(IV) in which A, B, W, X, Y, Z and R⁸ are each as defined above arecyclized intramolecularly in the presence of an acid and, ifappropriate, in the presence of a diluent.

[0757] Suitable diluents for the process (C) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore halogenatedhydrocarbons such as dichloromethane, chloroform, ethylene chloride,chlorobenzene, dichlorobenzene, moreover polar solvents, such asdimethyl sulphoxide, sulpholane, dimethyl formamide andN-methyl-pyrrolidone. Furthermore, it is possible to employ alcoholssuch as methanol, ethanol, propanol, iso-propanol, butanol, isobutanol,tert-butanol.

[0758] If appropriate, the acid used can also serve as diluent.

[0759] Suitable acids for the process (C) according to the invention areall customary inorganic and organic acids, such as, for example,hydrohalic acids, sulphuric acid, alkyl, aryl and haloalkylsulphonicacids, in particular halogenated alkylcarboxylic acids, such as, forexample, trifluoroacetic acid.

[0760] When carrying out the process (C) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

[0761] The process (C) according to the invention is generally carriedout under atmospheric pressure.

[0762] When carrying out the process (C) according to the invention, thereaction components of the formula (IV) and the acid are employed, forexample, in equimolar amounts. However, it is also possible, ifappropriate, to use the acid as solvent or as catalyst.

[0763] The processes (D-α) and (D-β) are characterized in that compoundsof the formula (V) or (VI) in which X, Y, Z, R⁸ and Hal are each asdefined above are reacted with compounds of the formula (VII) in which Aand D are each as defined above, if appropriate in the presence of abase and if appropriate in the presence of a diluent.

[0764] Suitable diluents for the processes (D-α) and (D-β) according tothe invention are all inert organic solvents. Preference is given tousing hydrocarbons, such as toluene and xylene, furthermore ethers, suchas dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone, andalso, only in the case where compounds of the formula (VI) are employed,alcohols such as methanol, ethanol, propanol, iso-propanol, butanol,iso-butanol and tert-butanol.

[0765] When compounds of the formula (V) are employed, suitable basesare inorganic bases, in particular alkali metal or alkaline earth metalcarbonates such as sodium carbonate, potassium carbonate or calciumcarbonate, and also organic bases, such as, for example, pyridine ortriethylamine, and when compounds of the formula (VI) are employed,alkali metal and alkaline earth metal oxides, hydroxides and carbonates,such as sodium hydroxide, potassium hydroxide, magnesium hydroxide,calcium oxide, sodium carbonate, potassium carbonate and calciumcarbonate, which can also be employed in the presence of phase-transfercatalysts, such as, for example, triethylbenzylammonium chloride,tetrabutylammonium bromide, Adogen 464 (=methyltrialkyl(C₈-C₁₀)-ammoniumchloride) or TDA 1 (=tris-(methoxyethoxyethyl)-amine), furthermorealkali metals, such as sodium or potassium, alkali metal amides andhydrides and alkaline earth metal amides and hydrides, such as sodiumamide, sodium hydride and calcium hydride, and additionally alkali metalalkoxides, such as sodium methoxide and potassium tertbutoxide.

[0766] When carrying out the processes (D-α) and (D-β) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the reaction is carried out at temperaturesbetween −20° C. and 250° C., preferably between 0° C. and 150° C.

[0767] The processes (D-α) and (D-β) according to the invention aregenerally carried out under atmospheric pressure.

[0768] When carrying out the processes (D-α) and (D-β) according to theinvention, the reaction components of the formulae (V) and (VII) or (VI)and (VII) and the deprotonating bases which are employed if appropriateare generally employed in approximately equimolar amounts. However, itis also possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

[0769] The process (E) according to the invention is characterized inthat carbonyl compounds of the formula (VIII) or enol ethers thereof ofthe formula (VIII-a) are reacted with ketene acid halides of the formula(V) in the presence of a diluent and, if appropriate, in the presence ofan acid acceptor.

[0770] Suitable diluents for the process (E) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, glycol dimethyl ether and diglycol dimethyl ether,moreover polar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide or N-methyl-pyrrolidone.

[0771] Suitable acid acceptors for carrying out the process variant E)according to the invention are all customary acid acceptors.

[0772] Preference is given to using tertiary amines, such astriethylamine, pyridine, diazabicyclooctane (DABCO),diazabicycloundecane (DBU), diazabicyclononene (DBN), Hünig base andN,N-dimethyl-aniline.

[0773] When carrying out the process variant E) according to theinvention, the reaction temperatures can be varied within a relativelywide range. Advantageously, the reaction is carried out at temperaturesbetween 0° C. and 250° C., preferably between 50° C. and 220° C.

[0774] The process (E) according to the invention is advantageouslycarried out under atmospheric pressure.

[0775] When carrying out the process (E) according to the invention, thereaction components of the formulae (VIII) and (V) in which A, D, X, Yand Z are each as defined above and Hal represents halogen, and, ifappropriate, the acid acceptors, are generally employed in approximatelyequimolar amounts. However, it is also possible to use a relativelylarge excess (up to 5 mol) of one component or the other.

[0776] The process (F) according to the invention is characterized inthat thioamides of the formula (IX) are reacted with ketene acid halidesof the formula (V) in the presence of a diluent and, if appropriate, inthe presence of an acid acceptor.

[0777] Suitable diluents for the process variant F) according to theinvention are all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, glycol dimethyl ether and diglycol dimethyl ether,moreover polar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide and N-methyl-pyrrolidone.

[0778] Suitable acid acceptors for carrying out the process (F)according to the invention are all customary acid acceptors.

[0779] Preference is given to using tertiary amines, such astriethylamine, pyridine, diazabicyclooctane (DABCO),diazabicycloundecane (DBU), diazabicyclononene (DBN), Hünig base andN,N-dimethyl-aniline.

[0780] When carrying out the process (F) according to the invention, thereaction temperatures can be varied within a relatively wide range.Advantageously, the reaction is carried out at temperatures between 0°C. and 250° C., preferably between 20° C. and 220° C.

[0781] The process (F) according to the invention is advantageouslycarried out under atmospheric pressure.

[0782] When carrying out the process (F) according to the invention, thereaction components of the formulae (IX) and (V) in which A, X, Y and Zare each as defined above and Hal represents halogen, and, ifappropriate, the acid acceptors, are generally employed in approximatelyequimolar amounts. However, it is also possible to use a relativelylarge excess (up to 5 mol) of one component or the other.

[0783] The process (G) is characterized in that compounds of the formula(X) in which A, B, Q¹, Q², Y, Z and R⁸ are each as defined above aresubjected to an intramolecular condensation in the presence of a base.

[0784] Suitable diluents for the process (G) according to the inventionare all organic solvents which are inert towards the reactionparticipants. Preference is given to using hydrocarbons, such as tolueneand xylene, furthermore ethers, such as dibutyl ether, tetrahydrofuran,dioxane, glycol dimethyl ether and diglycol dimethyl ether, moreoverpolar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide and N-methyl-pyrrolidone. It is furthermore possibleto use alcohols, such as methanol, ethanol, propanol, iso-propanol,butanol, isobutanol, tertbutanol.

[0785] Suitable bases (deprotonating agents) for carrying out theprocess (G) according to the invention are all customary protonacceptors. Preference is given to using alkali metal and alkaline earthmetal oxides, hydroxides and carbonates, such as sodium hydroxide,potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate,potassium carbonate and calcium carbonate, which can also be employed inthe presence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium orpotassium can also be used. Furthermore, alkali metal and alkaline earthmetal amides and hydrides, such as sodium amide, sodium hydride andcalcium hydride, and additionally also alkali metal alkoxides, such assodium methoxide, sodium ethoxide and potassium tert-butoxide can beemployed.

[0786] When carrying the process (G) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between −75° C. and250° C., preferably between −50° C. and 150° C.

[0787] The process (G) according to the invention is generally carriedout under atmospheric pressure.

[0788] When carrying out the process (G) according to the invention, thereaction components of the formula (X) and the deprotonating bases aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

[0789] The process (H) is characterized in that compounds of the formula(XI) in which A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y, Z and R⁸ are each as definedabove are subjected to an intramolecular condensation in the presence ofbases.

[0790] Suitable diluents for the process (H) according to the inventionare all organic solvents which are inert towards the reactionparticipants. Preference is given to using hydrocarbons, such as tolueneand xylene, furthermore ethers, such as dibutyl ether, tetrahydrofuran,dioxane, glycol dimethyl ether and diglycol dimethyl ether, moreoverpolar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide and N-methyl-pyrrolidone. Alcohols, such as methanol,ethanol, propanol, iso-propanol, butanol, isobutanol and tert-butanolcan also be used.

[0791] Suitable bases (deprotonating agents) for carrying out theprocess (H) according to the invention are all customary protonacceptors. Preference is given to using alkali metal and alkaline earthmetal oxides, hydroxides and carbonates, such as sodium hydroxide,potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate,potassium carbonate and calcium carbonate, which can also be employed inthe presence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium andpotassium can also be used. Furthermore, alkali metal and alkaline earthmetal amides and hydrides, such as sodium amide, sodium hydride andcalcium hydride, and additionally also alkali metal alkoxides, such assodium methoxide, sodium ethoxide and potassium tert-butoxide can beemployed.

[0792] When carrying the process (H) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

[0793] The process (H) according to the invention is generally carriedout under atmospheric pressure.

[0794] When carrying out the process (H) according to the invention, thereaction components of the formula (XII) and the deprotonating bases aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

[0795] For carrying out the process (I) according to the invention,palladium(0) complexes are suitable as catalysts. Use is made, forexample, of tetrakis(triphenylphosphine)palladium. Also suitable arepalladium(II) compounds such as bis(triphenylphosphine)palladium(II)chloride.

[0796] Suitable acid acceptors for carrying out the process (I)according to the invention are inorganic or organic bases. Thesepreferably include alkaline earth metal or alkali metal hydroxides,acetates, carbonates or bicarbonates, such as, for example, sodiumhydroxide, potassium hydroxide, barium hydroxide or ammonium hydroxide,sodium acetate, potassium acetate, calcium acetate or ammonium acetate,sodium carbonate, potassium carbonate or ammonium carbonate, sodiumbicarbonate or potassium bicarbonate, alkali metal fluorides, such as,for example, potassium fluoride, caesium fluoride, and also tertiaryamines, such as trimethylamine, triethylamine, tributylamine,N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine,N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) ordiazabicycloundecene (DBU).

[0797] Suitable diluents for carrying out the process (I) according tothe invention are water, organic solvents and any mixtures thereof.Examples include: aliphatic, alicyclic or aromatic hydrocarbons, suchas, for example, petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; halogenatedhydrocarbons, such as, for example, chlorobenzene, dichlorobenzene,methylene chloride, chloroform, carbon tetrachloride, dichloroethane,trichloroethane or tetrachloroethylene; ethers, such as diethyl ether,diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, diethyleneglycol dimethyl ether or anisole; alcohols, such as methanol, ethanol,n- or i-propanol, n-, iso-, sec- or tert-butanol, ethanediol,propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycolmonomethyl ether, diethylene glycol monoethyl ether; water.

[0798] The reaction temperature in the process (I) according to theinvention can be varied within a relatively wide range. In general, thereaction is carried out at temperatures between 0° C. and +140° C.,preferably between 50° C. and +100° C.

[0799] When carrying out the process (I) according to the invention,boronic acid of the formula (XII) and compounds of the formulae (I-1-a)to (I-8-a) are employed in a molar ratio of from 1:1 to 3:1, preferablyfrom 1:1 to 2:1. In general, 0.005 to 0.5 mol, preferably 0.01 mol to0.1 mol of catalyst is employed per mole of the compounds of theformulae (I-1-a) to (I-8-a). The base is usually employed in excess.

[0800] The process (J-α) is characterized in that compounds of theformulae (I-1-a) to (I-8-a) are in each case reacted with carbonylhalides of the formula (XIII), if appropriate in the presence of adiluent and if appropriate in the prescence of an acid binder.

[0801] Suitable diluents for the process (J-α) according to theinvention are all solvents which are inert towards the acyl halides.Preference is given to using hydrocarbons, such as benzine, benzene,toluene, xylene and tetralin, furthermore halogenated hydrocarbons, suchas methylene chloride, chloroform, carbon tetrachloride, chlorobenzeneand o-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such as dimethylsulphoxide and sulpholane. The hydrolytic stability of the acyl halidepermitting, the reaction can also be carried out in the presence ofwater.

[0802] Suitable acid binders for the reaction according to the process(J-α) according to the invention are all customary acid acceptors.Preference is given to using tertiary amines, such as triethylamine,pyridine, diazabicyclooctane (DABCO), diazabicyclo-undecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethyl-aniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, moreover alkali metal and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal hydroxides such as sodium hydroxide andpotassium hydroxide.

[0803] The reaction temperatures in the process (J-α) according to theinvention can be varied within a relatively wide range. In general, thereaction is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

[0804] When carrying out the process (J-α) according to the invention,the starting materials of the formulae (I-1-a) to (I-8-a) and thecarbonyl halide of the formula (XIII) are generally in each caseemployed in approximately equivalent amounts. However, it is alsopossible to employ a relatively large excess (up to 5 mol) of thecarbonyl halide. Work-up is carried out by customary methods.

[0805] The process (J-β) is characterized in that compounds of theformulae (I-1-a) to (I-8-a) are reacted with carboxylic anhydrides ofthe formula (XIV), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

[0806] Preferred diluents for the process (J-β) according to theinvention are those diluents which are also preferred when acyl halidesare used. Otherwise, it is also possible for a carboxylic anhydrideemployed in excess to act simultaneously as a diluent.

[0807] In the process (J-β), acid binders which are added, ifappropriate, are preferably those acid binders which are also preferredwhen acyl halides are used.

[0808] In the process (J-β) according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the reaction is carried out at temperatures between −20° C. and +150°C., preferably between 0° C. and 100° C.

[0809] When carrying out the process (J-β) according to the invention,the starting materials of the formulae (I-1-a) to (I-8-a) and thecarboxylic anhydride of the formula (XIV) are generally each employed inapproximately equivalent amounts. However, it is also possible to use arelatively large excess (up to 5 mol) of the carboxylic anhydride.Work-up is carried out by customary methods.

[0810] In general, the adopted procedure is to remove diluent and excesscarboxylic anhydride and also the carboxylic acid formed by distillationor by washing with an organic solvent or with water.

[0811] The process (K) is characterized in that compounds of theformulae (I-1-a) to (I-8-a) are in each case reacted with chloroformicesters or chloroformic thiol esters of the formula (XV), if appropriatein the presence of a diluent and if appropriate in the presence of anacid binder.

[0812] Suitable diluents for the reaction according to the process (K)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,DABCO, DBU, DBA, Hünig base and N,N-dimethyl-aniline, furthermorealkaline earth metal oxides, such as magnesium oxide and calcium oxide,moreover alkali metal carbonates and alkaline earth metal carbonates,such as sodium carbonate, potassium carbonate and calcium carbonate, andalso alkali metal hydroxides such as sodium hydroxide and potassiumhydroxide.

[0813] Suitable diluents for the process (K) according to the inventionare all solvents which are inert towards the chloroformic esters orchloroformic thiol esters. Preference is given to using hydrocarbons,such as benzine, benzene, toluene, xylene and tetralin, furthermorehalogenated hydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylicesters, such as ethyl acetate, and also strongly polar solvents, such asdimethyl sulphoxide and sulpholane.

[0814] When carrying out the process (K) according to the invention thereaction temperatures can be varied within a relatively wide range. Ifthe reaction is carried out in the presence of a diluent and an acidbinder, the reaction temperatures are generally between −20° C. and+100° C., preferably between 0° C. and 50° C.

[0815] The process (K) according to the invention is generally carriedout under atmospheric pressure.

[0816] When carrying out the process (K) according to the invention, thestarting materials of the formulae (I-1-a) to (I-8-a) and theappropriate chloroformic ester or chloroformic thiol ester of theformula (XV) are generally in each case employed in approximatelyequivalent amounts. However, it is also possible to employ a relativelylarge excess (up to 2 mol) of one component or the other. Work-up iscarried out by customary methods. In general, precipitated salts areremoved and the reaction mixture that remains is concentrated bystripping the diluent.

[0817] The process (L) according to the invention is characterized inthat compounds of the formulae (I-1-a) to (I-8-a) are in each casereacted with compounds of the formula (XVI) in the presence of a diluentand, if appropriate, in the presence of an acid binder.

[0818] In the preparation process (L), approximately 1 mol ofchloromonothioformic ester or chlorodithioformic ester of the formula(XVI) is reacted per mole of starting material of the formulae (I-1-a)to (I-8-a), at from 0 to 120° C., preferably from 20 to 60° C.

[0819] Suitable diluents which are added if appropriate are all inertpolar organic solvents, such as ethers, amides, sulphones, sulphoxides,but also halogenoalkanes.

[0820] Preference is given to using dimethyl sulphoxide,tetrahydrofuran, dimethylformamide or methylene chloride.

[0821] If, in a preferred embodiment, the enolate salt of the compounds(I-1-a) to (I-8-a) is prepared by addition of strong deprotonatingagents, such as, for example, sodium hydride or potassium tert-butoxide,it is not necessary to add further acid binders.

[0822] If acid binders are employed, these are customary inorganic ororganic bases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine, triethylamine.

[0823] The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

[0824] The process (M) according to the invention is characterized inthat compounds of the formulae (I-1-a) to (I-8-a) are in each casereacted with sulphonyl chlorides of the formula (XVII), if appropriatein the presence of a diluent and if appropriate in the presence of anacid binder.

[0825] In the preparation process (M), approximately 1 mol of sulphonylchloride of the formula (XVII) is reacted per mole of starting materialof the formula (I-1-a) to (I-8-a), at from −20 to 150° C., preferably atfrom 20 to 70° C. um.

[0826] Suitable diluents which are added if appropriate are all inertpolar organic solvents, such as ethers, amides, nitrites, sulphones,sulphoxides or halogenated hydrocarbons, such as methylene chloride.

[0827] Preference is given to using dimethyl sulphoxide,tetrahydrofuran, dimethylformamide, methylene chloride.

[0828] If, in a preferred embodiment, the enolate salt of the compounds(I-1-a) to (I-8-a) is prepared by addition of strong deprotonatingagents (such as, for example, sodium hydride or potassiumtert-butoxide), it is not necessary to add further acid binders.

[0829] If acid binders are employed, these are customary inorganic ororganic bases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine, triethylamine.

[0830] The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

[0831] The process (N) according to the invention is characterized inthat compounds of the formulae (I-1-a) to (I-8-a) are in each casereacted with phosphorus compounds of the formula (XVIII), if appropriatein the presence of a diluent and if appropriate in the presence of anacid binder.

[0832] In the preparation process (N), 1 to 2, preferably 1 to 1.3, molof the phosphorus compound of the formula (XVIII) are reacted per moleof the compounds (I-1-a) to (I-8-a) at temperatures between −40° C. and150° C., preferably between −10 and 110° C., to give compounds of theformulae (I-1-e) to (I-8-e).

[0833] Suitable solvents which are added if appropriate are all inertpolar organic solvents, such as ethers, amides, nitrites, alcohols,sulphides, sulphones, sulphoxides, etc.

[0834] Preference is given to using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethylformamide, methylene chloride.

[0835] Suitable acid binders which are added if appropriate arecustomary inorganic or organic bases such as hydroxides, carbonates oramines. Examples include sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine, triethylamine.

[0836] The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods of organicchemistry. The resulting end products are preferably purified bycrystallization, chromatographic purification or by so-called “incipientdistillation”, i.e. removal of the volatile components under reducedpressure.

[0837] The process (O) is characterized in that compounds of the formula(I-1-a) to (I-8-a) are reacted with metal hydroxides or metal alkoxidesof the formula (XIX) or amines of the formula (XX), if appropriate inthe presence of a diluent.

[0838] Preferred diluents for the process (O) according to the inventionare ethers, such as tetrahydrofuran, dioxane, diethyl ether, or elsealcohols, such as methanol, ethanol, isopropanol, but also water.

[0839] The process (O) according to the invention is generally carriedout under atmospheric pressure.

[0840] The reaction temperatures are generally between −20° C. and 100°C., preferably between 0° C. and 50° C.

[0841] The process (P) according to the invention is characterized inthat compounds of the formulae (I-1-a) to (I-8-a) are in each casereacted with (P-α) compounds of the formula (XXI), if appropriate in thepresence of a diluent and if appropriate in the presence of a catalyst,or (P-β) with compounds of the formula (XII), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

[0842] In the preparation process (P-α), approximately one mol ofisocyanate of the formula (XXI) is reacted per mole of starting materialof the formulae (I-1-a) to (I-8-a), at from 0 to 100° C., preferably atfrom 20 to 50° C.

[0843] Suitable diluents which are added if appropriate are all inertorganic solvents, such as ethers, amides, nitriles, sulphones,sulphoxides.

[0844] If appropriate, catalysts may be added to accelerate thereaction. Very advantageously, the catalysts which are employed areorganotin compounds, such as, for example, dibutyltin dilaurate. Thereaction is preferably carried out at atmospheric pressure.

[0845] In the preparation process (P-β), approximately 1 mol ofcarbamoyl chloride of the formula (XXII) is reacted per mole of startingmaterial of the formulae (I-1-a) to (I-8-a), at from −20 to 150° C.,preferably from 0 to 70° C. um.

[0846] Suitable diluents which are added if appropriate are all inertpolar organic solvents, such as ethers, amides, sulphones, sulphoxidesor halogenated hydrocarbons.

[0847] Preference is given to using dimethyl sulphoxide,tetrahydrofuran, dimethylformamide or methylene chloride.

[0848] If, in a preferred embodiment, the enolate salt of the compounds(I-1-a) to (I-8-a) is prepared by addition of strong deprotonatingagents (such as, for example, sodium hydride or potassiumtert-butoxide), it is not necessary to add further acid binders.

[0849] If acid binders are employed, these are customary inorganic ororganic bases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, triethylamine or pyridine.

[0850] The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

[0851] The active compounds are suitable for controlling animal pests,in particular insects, arachnids and nematodes, which are encountered inagriculture, in forestry, in the protection of stored products and ofmaterials, and in the hygiene sector, and have good plant tolerance andfavourable toxicity to warm-blooded animals. They may be preferablyemployed as plant protection agents. They are active against normallysensitive and resistant species and against all or some stages ofdevelopment. The abovementioned pests include:

[0852] From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

[0853] From the order of the Diplopoda, for example, Blaniulusguttulatus.

[0854] From the order of the Chilopoda, for example, Geophiluscarpophagus and Scutigera spp.

[0855] From the order of the Symphyla, for example, Scutigerellaimmaculata.

[0856] From the order of the Thysanura, for example, Lepisma saccharina.

[0857] From the order of the Collembola, for example, Onychiurusarmatus.

[0858] From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

[0859] From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

[0860] From the order of the Dermaptera, for example, Forficulaauricularia.

[0861] From the order of the Isoptera, for example, Reticulitermes spp.

[0862] From the order of the Phthiraptera, for example, Pediculushumanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp.and Damalinia spp.

[0863] From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

[0864] From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

[0865] From the order of the Homoptera, for example, Aleurodesbrassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii,Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi,Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix,Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli,Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettixcincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus,Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae,Pseudococcus spp. and Psylla spp.

[0866] From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus Spp,

[0867] From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis and Costelytra zealandica.

[0868] From the order of the Hymenoptera, for example, Diprion spp.,Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

[0869] From the order of the Diptera, for example, Aedes spp., Anophelesspp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp.,Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebraspp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

[0870] From the order of the Siphonaptera, for example, Xenopsyllacheopis and Ceratophyllus spp.

[0871] From the order of the Arachnida, for example, Scorpio maurus,Latrodectus mactans. Acarus siro, Argas spp., Omithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., Brevipalpus spp.

[0872] The phytoparasitic nematodes include, for example, Pratylenchusspp., Radopholus similis, Ditylenchus dipsaci, Tylenchulussemipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp.,Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.,Bursaphelenchus spp.

[0873] The active compounds according to the invention have highinsecticidal and acaridical activity after foliar and soil application.

[0874] They can be employed particularly successfully for controllingplant-damaging insects, such as, for example, against the larvae of themustard beetle (Phaedon cochleariae), against the larvae of the greenrice leafhopper (Nephotettix cincticeps) and against the larvae of thegreen peach aphid (Myzus persicae).

[0875] The active compounds can be converted to the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound and microencapsulationsin polymericsubstances.

[0876] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is, liquid solvents,and/or solid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants, and/or foam-formers.

[0877] If the extender used is water, it is also possible to employ forexample organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and also their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, and also water.

[0878] As solid carriers there are suitable:

[0879] for example ammonium salts and ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals, such as highlydisperse silica, alumina and silicates; as solid carriers for granulesthere are suitable: for example crushed and fractionated natural rockssuch as calcite, marble, pumice, sepiolite and dolomite, and alsosynthetic granules of inorganic and organic meals, and granules oforganic material such as sawdust, coconut shells, maize cobs and tobaccostalks; as emulsifiers and/or foam-formers there are suitable: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand also protein hydrolysates; as dispersants there are suitable: forexample lignin-sulphite waste liquors and methylcellulose.

[0880] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

[0881] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organicdyestuffs, such as alizarin dyestuffs, azo dyestuffs and metalphthalocyanine dyestuffs, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0882] The formulations generally comprise between 0.1 and 95% by weightof active compound, preferably between 0.5 and 90%.

[0883] The active compound according to the invention can be present inits commercially available formulations and in the use forms, preparedfrom these formulations, as a mixture with other active compounds, suchas insecticides, attractants, sterilizing agents, bactericides,acaricides, nematicides, fungicides, growth-regulating substances orherbicides. The insecticides include, for example, phosphoric acidesters, carbamates, carboxylates, chlorinated hydrocarbons, phenylureasand substances produced by microorganisms,inter alia.

[0884] Particularly favourable examples of co-components in mixtures arethe following compounds:

Fungicides

[0885] aldimorph, ampropylfos, ampropylfos potassium, andoprim,anilazine, azaconazole, azoxystrobin,

[0886] benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

[0887] calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

[0888] debacarb, dichlorophen, diclobutrazole, diclofluanid,diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol,dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine,dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

[0889] edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

[0890] famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram,fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate,fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

[0891] guazatine,

[0892] hexachlorobenzene,hexaconazole,hymexazole,

[0893] imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

[0894] kasugamycin, kresoxim-methyl, copper preparations, such as:copper hydroxide, copper naphthenate, copper oxychloride, coppersulphate, copper oxide, oxine-copper and Bordeaux mixture,

[0895] mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

[0896] nickel dimethyldithiocarbamate,nitrothal-isopropyl,nuarimol,ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

[0897] paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

[0898] quinconazole, quintozene (PCNB),

[0899] sulphur and sulphur preparations,

[0900] tebuconazole, tecloftalam, tecnazene, tetcyclasis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichiamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

[0901] uniconazole,

[0902] validamycin A, vinclozolin, viniconazole,

[0903] zarilamide, zineb, ziram and also

[0904] Dagger G,

[0905] OK-8705,

[0906] OK-8801 ,

[0907]α-1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

[0908]α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

[0909]α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

[0910]α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

[0911] (5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

[0912] (E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

[0913] 1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

[0914]1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,

[0915] 1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,

[0916] 1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,

[0917] 1-[(diiodomethyl)-sulphonyl]4-methyl-benzene,

[0918]1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

[0919]1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

[0920]1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

[0921] 1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

[0922]2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

[0923]2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

[0924] 2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

[0925] 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

[0926] 2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

[0927] 2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

[0928]2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

[0929]2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

[0930] 2-aminobutane,

[0931] 2-bromo-2-(bromomethyl)-pentanedinitrile,

[0932]2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden4-yl)-3-pyridinecarboxamide,

[0933]2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

[0934] 2-phenylphenol(OPP),

[0935] 3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrol-2,5-dione,

[0936]3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

[0937] 3-(1,1-dimethylpropyl-1-oxo-1H1-indene-2-carbonitrile,

[0938] 3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

[0939]4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

[0940] 4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

[0941]8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

[0942] 8-hydroxyquinoline sulphate,

[0943] 9H-xanthene-2- [(phenylamino)-carbonyl]-9-carboxylidydrazide,

[0944]bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-tophenedicarboxylate,

[0945] cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

[0946]cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

[0947] ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

[0948] potassium bicarbonate,

[0949] methanetetrathiol-sodiumsalt,

[0950] methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

[0951] methylN-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

[0952] methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

[0953] N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

[0954]N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

[0955]N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

[0956] N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

[0957] N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

[0958] N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

[0959]N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

[0960] N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,

[0961] N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

[0962]N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

[0963] N-formyl-N-hydroxy-DL-alanine-sodiumsalt,

[0964] O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

[0965] O-methyl S-phenyl phenylpropylphosphoramidothioate,

[0966] S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

[0967] spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,

Bactericides

[0968] bronopol, dichlorophen, nitrapyrin, nickeldimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid,oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphateand other copper preparations.

Insecticides/acaricides/nematicides

[0969] abamectin, acephate, acetamiprid, acrinathrin, alanycarb,aldicarb, aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz,avermectin, AZ 60541, azadirachtin, azamethiphos, azinphos A,azinphos-M, azocyclotin,

[0970] Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis,Bacillus thuringiensis, baculoviruses, Beauveria bassiana, Beauveriatenella, bendiocarb, benfuracarb, bensultap, benzoximate,betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin,BPMC, bromophos A, bufencarb, buprofezin, butathiofos, butocarboxim,butylpyridaben,

[0971] cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan,cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypermethrin, cyromazine,

[0972] deltamethirin, demeton M, demeton S, demeton-S-methyl,diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimethoate,dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn,

[0973] eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthoraspp., esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox,etoxazole, etrimfos,

[0974] fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad,fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazinam,fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,furathiocarb,

[0975] granulosis viruses,

[0976] halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,hydroprene,

[0977] imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

[0978] nuclear polyhedrosis viruses,

[0979] lambda-cyhalothrin, lufenuron,

[0980] malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, monocrotophos,

[0981] naled, nitenpyrarn, nithiazine, novaluron,

[0982] omethoate, oxamyl, oxydemethon M,

[0983] Paecilomyces filmosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur,prothiofos, prothoate, pymetrozine, pyraclofos, pyresmethrin, pyrethrum,pyridaben, pyridathion, pyrimidifen, pyriproxyfen,

[0984] quinalphos,

[0985] ribavirin,

[0986] salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,

[0987] tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, theta-cypermethrin, thiapronil, thiatriphos,thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringiensin,tralocythrin, tralomethrin, triarathene, triazamate, triazophos,triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb,

[0988] vamidothion, vaniliprole, Verticillium lecanii,

[0989] YI 5302,

[0990] zeta-cypermethrin, zolaprofos,

[0991](1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

[0992](3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,

[0993]1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

[0994]2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

[0995] 2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,

[0996]2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

[0997]2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

[0998] 3-methylphenyl propylcarbamate.

[0999] 4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

[1000]4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

[1001]4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

[1002]4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

[1003] Bacillus thuringiensis strain EG-2348,

[1004] [2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

[1005]2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[1006][3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

[1007] dihydro-2-(nitromethylene)-2H-1,3-thiazine-3 (4H)-carboxaldehyde,

[1008] ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

[1009] N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

[1010]N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

[1011] N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

[1012] N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

[1013] N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

[1014] O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

[1015] It is also possible to admix other known active compounds, suchas herbicides, fertilizers and growth regulators.

[1016] When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergistic agents are compoundswhich increase the action of the active compounds, without it beingnecessary for the synergistic agent added to be active itself.

[1017] The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

[1018] The compounds are employed in a customary manner appropriate forthe use forms.

[1019] When used against hygiene pests and pests of stored products, theactive compound is distinguished by an excellent residual action on woodand clay as well as a good stability to alkali on limed substrates.

[1020] The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.By weeds in the broadest sense, there are to be understood all plantswhich grow in locations where they are not wanted. Whether thesubstances according to the invention act as total or selectiveherbicides depends essentially on the amount used.

[1021] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[1022] Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus andTaraxacum.

[1023] Dicotyledonous cultures of the genera: Gossypium, Glycine, Beta,Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

[1024] Monocotyledonous weeds of the genera: Echinochloa, Setaria,Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium,Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria,Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum,Sphenoclea, Dactyloctenium, Agrostis, Alopecurus Apera, Aegilopus andPhalaris.

[1025] Monocotyledonous cultures of the genera: Oryza, Zea, Triticum,Hordeum, Avena, Secale, Sorghum, Panicum, Saccharurn, Ananas, Asparagusand Allium.

[1026] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[1027] The compounds are suitable, depending on the concentration, forthe total control of weeds, for example on industrial terrain andrailway tracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for the control of weeds inperennial crops for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, inlawns, turf and pasture-land, and for the selective control of weeds inannual crops.

[1028] The compounds of the formula (I) according to the invention havestrong herbicidal activity and a broad activity spectrum when applied tothe soil and to the above-ground parts of the plants. To a certainextent, they are also suitable for the selective control ofmonocotyledonous and dicotyledonous weeds in moncotyledonous anddicotyledonous crops, both pre-emergence and post-emergence.

[1029] For the control of weeds, the active compounds according to theinvention, as such or in the form of their formulations, can also beused as mixtures with known herbicides, finished formulations or tankmixes being possible.

[1030] Possible components for the mixtures are known herbicides, forexample

[1031] acetochlor, acifluorfen(-sodium), aclonifen, alachlor,alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafanedin, azimsulfuron, benazolin(-ethyl),benfuiresate, bensulfuron(-methyl), bentazon, benzofenap,benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium),bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl),chlornitrofen, chlorsulfuron, chlortoluron, cinidon(-ethyl),cinmethylin, cinosulfuron, clethodim, clodinafop(-propargyl), clomazone,clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam(-methyl),cumyluron, cyanazine, cybutryne, cycloate, cyclosulfarnuron, cycloxydim,cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate,dicamba, diclofop(-methyl), diclosularn, diethathyl(-ethyl),difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate,dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine,diphenamid, diquat, dithiopyr, diuron, dynron, epoprodan, EPTC,esprocarb, ethalfluralin, ethametsulfuron(-methyl), ethofumesate,ethoxyfen, etobenzanid, fenoxaprop(-P-ethyl), flamprop(-isopropyl),flarnprop(-isopropyl-L), flamprop(-methyl), flazasulfuron,fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam,flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam,fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam,flupropacil, flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl),fluridone, fluroxypyr(-meptyl), flurprimidol, flurtamone,fluciathet(-methyl), fluthiamide, fomesafen, glufosinate(-ammonium),glyphosate(-isopropylanmmonium), halosafen, ihaloxyfop (-ethoxyethyl),haloxyfop(-P-methyl), hexazinone, imazamethabenz(-methyl),imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr,imazosulfuron, iodosulfuron, ioxynil, isopropalin, isoproturon, isouron,isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil,linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor,methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor,metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate,monolinuron, naproanilide, napropamide, neburon, nicosulfuron,norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuiron,oxaziclomefone, oxyfluorfen, paraquat, perlagon acid, pendimethalin,pentoxazone, phenmedipham, piperophos, pretilachlor,prinisulfuron(-methyl), prometryn, propachlor, propanil, propaquizafop,propisochlor, propyzamide, prosulfocarb, prosulfuron,pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen,pyribenzoxim, pyributicarb, pyridate, pyriminobac(-methyl),pyrithiobac(-sodium), quinchlorac, quinrerac, quinoclamine,quizalofop(-ethyl), quizalofop(-p-tefuryl), rimsulfuron, sethoxydim,simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl),sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr,tridiphane, trifluralin and triflusulfuron.

[1032] Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, are also possible.

[1033] The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

[1034] The active compounds according to the invention can be appliedeither before or after emergence of the plants. They can also beincorporated into the soil before sowing.

[1035] The amount of active compound used can vary within a substantialrange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

[1036] The active compounds according to the invention act not onlyagainst plant, hygiene and stored product pests, but also in theveterinary medicine sector against animal parasites (ectoparasites),such as hard ticks, soft ticks, mange mites, leaf mites, flies (bitingand licking), parasitic fly larvae, lice, hair lice, feather lice andfleas. These parasites include:

[1037] From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

[1038] From the order of the Mallophagida and the suborders Amblycerinaand Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinotonspp., Bovicola spp., Wemeckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

[1039] From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

[1040] From the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

[1041] From the order of the Heteropterida, for example, Cimex spp.,Triatoma spp., Rhodnius spp. and Panstrongylus spp.

[1042] From the order of the Blattarida, for example Blatta orientalis,Periplaneta armericana, Blattela germanica and Supella spp.

[1043] From the subclass of the Acaria (Acarida) and the orders of theMeta- and Mesostigmata, for example, Argas spp., Ornithodorus spp.,Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentorspp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssusspp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroaspp.

[1044] From the order of the Actinedida (Prostigmata) und Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

[1045] The active compounds of the formula (I) according to theinvention are also suitable for controlling arthropods which infestagricultural productive livestock, such as, for example, cattle, sheep,goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens,turkeys, ducks, geese and bees, other pets, such as, for example, dogs,cats, caged birds and aquarium fish, and also so-called test animals,such as, for example, hamsters, guinea pigs, rats and mice. Bycontrolling these arthropods, cases of death and reduction inproductivity (for meat, milk, wool, hides, eggs, honey etc.) should bediminished, so that more economic and easier animal husbandry ispossible by use of the active compounds according to the invention.

[1046] The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of molded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

[1047] When used for cattle, poultry, pets and the like, the activecompounds of the formula (I) can be used as formulations (for examplepowders, emulsions, free-flowing compositions), which comprise theactive compounds in an amount of 1 to 80% by weight, directly or after100 to 10 000-fold dilution, or they can be used as a chemical bath.

[1048] It has furthermore been found that the compounds of the formula(I) according to the invention also have a strong insecticidal actionagainst insects which destroy industrial materials.

[1049] The following insects may be mentioned as examples and aspreferred—but without a limitation:

[1050] Beetles, such as

[1051]Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum,Xestobium rufovillosum, Ptilinus pecticomis, Dendrobium pertinex,Emobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus,Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylonaequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apatemonachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylonspec. Dinoderus minutus.

[1052] Hymenopterons, such as

[1053]Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerusaugur

[1054] Termites, such as

[1055]Kalotermes flavicollis, Cryptotermes brevis, Heterotermesindicola, Reticulitermes flavipes, Reticulitermes santonensis,Reticulitermes lucifugus, Mastotermes darwiniensis, Zooternopsisnevadensis, Coptotermes formosanus.

[1056] Bristletails, such as

[1057]Lepisma saccarina.

[1058] Industrial materials in the present connection are to beunderstood as meaning non-living materials, such as, preferably,plastics, adhesives, sizes, papers and cards, leather, wood andprocessed wood products and coating compositions.

[1059] Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

[1060] Wood and wood processed wood products which can be protected bythe agents according to the invention or mixtures comprising these areto be understood as meaning, for example: building timber, wooden beams,railway sleepers, bridge components, boat jetties, wooden vehicles,boxes, pallets, containers, telegraph poles, wood panelling, woodenwindows and doors, plywood, chipboard, joinery or wooden products whichare used quite generally in house-building or in building joinery.

[1061] The active compounds can be used as such, in the form ofconcentrates or in generally customary formulations, such as powders,granules, solutions, suspensions, emulsions or pastes.

[1062] The formulations mentioned can be prepared in a manner known perse, for example by mixing the active compounds with at least one solventor diluent, emulsifier, dispersing agent and/or binder or fixing agent,a water repellent, if appropriate siccatives and UV stabilizers and ifappropriate dyestuffs and pigments, and also other processingauxiliaries.

[1063] The insecticidal compositions or concentrates used for thepreservation of wood and wood-derived timber products comprise theactive compound according to the invention in a concentration of 0.0001to 95% by weight, in particular 0.001 to 60% by weight.

[1064] The amount of the compositions or concentrates employed dependson the nature and occurrence of the insects and on the medium. Theoptimum amount employed can be determined for the use in each case by aseries of tests. In general, however, it is sufficient to employ 0.0001to 20% by weight, preferably 0.001 to 10% by weight, of the activecompound, based on the material to be preserved.

[1065] Solvents and/or diluents which are used are an organic chemicalsolvent or solvent mixture and/or an oily or oil-like organic chemicalsolvent or solvent mixture of low volatility and/or a polar organicchemical solvent or solvent mixture and/or water, and if appropriate anemulsifier and/or wetting agent.

[1066] Organic chemical solvents which are preferably used are oily oroil-like solvents having an evaporation number above 35 and a flashpointabove 30° C., preferably above 45° C. Substances which are used as suchoily or oil-like water-insoluble solvents of low volatility areappropriate mineral oils or aromatic fractions thereof, or solventmixtures containing mineral oils, preferably white spirit, petroleumand/or alkylbenzene.

[1067] Mineral oils having a boiling range from 170 to 220° C., whitespirit having a boiling range from 170 to 220° C., spindle oil having aboiling range from 250 to 350° C., petroleum and aromatics having aboiling range from 160 to 280° C., terpentine oil and the like, areadvantageously employed.

[1068] In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferably(x-monochloronaphthalene, are used.

[1069] The organic oily or oil-like solvents of low volatility whichhave an evaporation number above 35 and a flashpoint above 30° C.,preferably above 45° C., can be replaced in part by organic chemicalsolvents of high or medium volatility, providing that the solventmixture likewise has an evaporation number above 35 and a flashpointabove 30° C., preferably above 45° C., and that theinsecticide/fungicide mixture is soluble or emulsifiable in this solventmixture.

[1070] According to a preferred embodiment, some of the organic chemicalsolvent or solvent mixture is replaced by an aliphatic polar organicchemical solvent or solvent mixture. Aliphatic organic chemical solventscontaining hydroxyl and/or ester and/or ether groups, such as, forexample, glycol ethers, esters or the like, are preferably used.

[1071] Organic chemical binders which are used in the context of thepresent invention are the synthetic resins and/or binding drying oilswhich are known per se, are water-dilutable and/or are soluble ordispersible or emulsifiable in the organic chemical solvents employed,in particular binders consisting of or comprising an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenolic resin, hydrocarbon resin, such asindene-cumarone resin, silicone resin, drying vegetable oils and/ordrying oils and/or physically drying binders based on a natural and/orsynthetic resin.

[1072] The synthetic resin used as the binder can be employed in theform of an emulsion, dispersion or solution. Bitumen or bituminoussubstances can also be used as binders in an amount of up to 10% byweight. Dyestuffs, pigments, water-repelling agents, odour correctantsand inhibitors or anticorrosive agents and the like which are known perse can additionally be employed.

[1073] It is preferred according to the invention for the composition orconcentrate to comprise, as the organic chemical binder, at least onealkyd resin or modified alkyd resin and/or one drying vegetable oil.Alkyd resins having an oil content of more than 45% by weight,preferably 50 to 68% by weight, are preferably used according to theinvention.

[1074] All or some of the binder mentioned can be replaced by a fixingagent (mixture) or a plasticizer (mixture). These additives are intendedto prevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

[1075] The plasticizers originate from the chemical classes of phthalicacid esters, such as dibutyl, dioctyl or benzyl butyl phthalate,phosphoric acid esters, such as tributyl phosphate, adipic acid esters,such as di-(2-ethylhexyl) adipate, stearates, such as butyl stearate oramyl stearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

[1076] Fixing agents are based chemically on polyvinyl alkyl ethers,such as, for example, polyvinyl methyl ether or ketones, such asbenzophenone or ethylenebenzophenone.

[1077] Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementioned organicchemical solvents or diluents, emulsifiers and dispersing agents.

[1078] Particularly effective preservation of wood is achieved byimpregnation processes on a large industrial scale, for example vacuum,double vacuum or pressure processes.

[1079] The ready-to-use compositions can also comprise otherinsecticides, if appropriate, and also one or more fungicides, ifappropriate.

[1080] Possible additional mixing partners are, preferably, theinsecticides and fungicides mentioned in WO 94/29 268. The compoundsmentioned in this document are an explicit constituent of the presentapplication.

[1081] Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethirin, permethrin, imidacloprid,NI-25, flufenoxuron, hexaflumuron and triflumuron, and also fungicides,such as epoxyconazole, hexaconazole, azaconazole, propiconazole,tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid,tolylfluanid, 3-iodo-2-propinyl-butyl carbamate,N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.

[1082] The preparation and the use of the active compounds according tothe invention is illustrated by the examples below.

EXAMPLE Myzus Test

[1083] Solvent: 1 part by weight of dimethylformamide Emulsifier: 1 partby weight of alkylaryl polyglycol ether

[1084] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[1085] Cabbage leaves (Brassica oleracea) which are heavily infested bypeach aphids (Myzus persicae) are treated by being dipped into thepreparation of active compound of the desired concentration.

[1086] After the desired period of time, the kill in % is determined.100% means that all aphids have been killed; 0% means that none of theaphids have been killed.

[1087] In this test, for example, the following compound of thePreparation Examples shows good activity: TABLE Plant-damaging insectsMyzus test Concentration of active compound Kill in % after Activecompound in % 6 days Ex. I-1-a-4 0.1 95

EXAMPLE Nephotettix Test

[1088] Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1part by weight of alkylaryl polyglycol ether

[1089] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[1090] Rice seedlings (Oryza sativa) are treated by being dipped intothe preparation of active compound of the desired concentration and arepopulated with larvae of the green rice leaf-hopper (Nephotettixcincticeps) while the leaves are still moist.

[1091] After the desired period of time, the kill in % is determined.100% means that all leaf-hoppers have been killed; 0% means that none ofthe leaf-hoppers have been killed.

[1092] In this test, for example, the following compounds of thePreparation Examples show good activity: TABLE Plant-damaging insectsNephotettix test Active compound Kill in % after Active compound in % 6days Ex. I-1-a-3 0.1 100

Ex. I-1-a-4 0.1 100

EXAMPLE Phaedon Larvae Test

[1093] Solvent: 7 parts by weights of dimethylformamide Emulsifier: 1part by weight of alkylaryl polyglycol ether

[1094] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[1095] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with larvae of the mustard beetle (Phaedon cochleariae)while the leaves are still moist.

[1096] After the desired period of time, the kill in % is determined.100% means that all aphids have been killed; 0% means that none of theaphids have been killed.

[1097] In this test, for example, the following compounds of thePreparation Examples shows good activity: TABLE Plant-damaging insectsPhaedon larvae test Concentration of active compound Kill in % after 7Active compound in % days Ex. I-1-a-3 0.1 100

Ex. I-1-a-4 0.1 100

EXAMPLE Post-emergence Test

[1098] Solvent: 5 parts by weight of acetone Emulsifier: 1 part byweight of alkylaryl polyglycol ether

[1099] To produce a suitable preparation of active compound, one part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[1100] Test plants which have a height of 5-15 cm are sprayed with thepreparation of active compound in such a way as to apply the particularamounts of active compound desired per unit area. After 3 weeks, thedegree of damage to the plants is rated in % damage in comparison to thedevelopment of the untreated control.

[1101] The figures denote:  0% = no effect (like untreated control) 100%= total destruction

[1102] Post-emergence/greenhouse Sugar Avena g of ai./ha beet fatuaSetaria Sinapis Ex. I-1-a-2 250 20  70 100 70 Avena g of ai./ha fatuaSetaria Abutilon Amaranthus Ex. I-1-a-4 250 90 100  80 80

EXAMPLE Pre-emergence Test

[1103] Solvent: 5 parts by weight of acetone Emulsifier: 1 part byweight of alkylaryl polyglycol ether

[1104] To produce a suitable preparation of active compound, one part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[1105] Seeds of the test plants are sown in normal soil and, after 24hours, watered with the preparation of the active compound.Advantageously, the amount of water per unit area is kept constant. Theactive compound concentration in the preparation is not important, onlythe active compound application rate per unit area matters. After threeweeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control.

[1106] The figures denote:  0% = no effect (like untreated control) 100%= total destruction

[1107] Pre-emergence/greenhouse g of ai./ha Alopecurus SetariaAmaranthus Galium Ex. I-1-a-3 250 100 100 100 90

EXAMPLE I-1-a-1

[1108]

[1109] Under argon, 1.1 g of3-[(4-bromo-2-ethyl-6-methyl)-phenyl]-5-isopropyl-5-methyl-pyrrolidin-2,4-dioneaccording to Example I-1-a-4 from WO 97/02243 in 20 ml of1,2-dimethoxyethane are admixed with 0.6 g of 4-chlorophenylboronic acidand 180 mg of tetrakis(triphenylphosphine)palladium. The mixture isstirred at 20° C. for 15 min, 15 ml of 20% strength aqueous sodiumcarbonate solution are then added, and the mixture is stirred at 80° C.for one day. The mixture is then filtered, the filtrate is admixed withwater and the aqueous phase is acidified. Filtration with suction gives0.75 g of product (65% of theory).

[1110] m.p.: 245° C.

[1111] By the method of Example (I-1-a-1) and (I-1-a-43), and/or inaccordance with the general procedures for preparing compounds of theformula (I-1-a), the following compounds of the formula (I-1-a) areobtained: (I-1-a)

Ex. No. X Z V¹ V² D A B m.p.° C. isomer I-1-a-2 CH₃ CH₃ 4-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— >240 β I-1-a-3 CH₃ Cl 4-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— 211 β I-1-a-4 CH₃ Cl 4-Cl H H—(CH₂)₂—CHOC₂H₅—(CH₂)₂— >230 β I-1-a-5 CH₃ CH₃ 4-Cl H H—CH₂—O—(CH₂)₃— >240 — I-1-a-6 C₂H₅ CH₃ 4-Cl H H CH₃ CH₃ >240 — I-1-a-7C₂H₅ C₂H₅ 4-Cl H H —(CH₂)₂—CHCH₃—(CH₂)₂— 188 β I-1-a-8 CH₃ Cl 4-Cl H H—(CH₂)₂—O—(CH₂)₂— 165-167 — I-1-a-9 C₂H₅ Cl 4-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— >240 β I-1-a-10 C₂H₅ Cl 4-Cl H H—(CH₂)₂—CHCH₃—(CH₂)₂— >240 β I-1-a-11 CH₃ Cl 4-Cl H H i-C₃H₇ CH₃ >240 —I-1-a-12 CH₃ CH₃ 4-Cl H H CH₃ CH₃ >240 — I-1-a-13 C₂H₅ C₂H₅ 4-Cl H Hi-C₃H₇ CH₃ 218 — I-1-a-14 CH₃ CH₃ 4-Cl H H —(CH₂)₅— >240 — I-1-a-15 CH₃CH₃ 3-Cl H H —(CH₂)₂—CHOCH₃—(CH₂)₂— 135 β I-1-a-16 CH₃ CH₃ 2-Cl H H—(CH₂)₂CHOCH₃(CH₂)₂— >245 β I-1-a-17 CH₃ CH₃ 4-Cl H H—(CH₂)₂—O—(CH₂)₂— >235 — I-1-a-18 CH₃ CH₃ 4-Cl H H—(CH₂)₂CHOC₂H₅(CH₂)₂— >245 β I-1-a-19 CH₃ CH₃ 4-Cl H H—(CH₂)₂—CHCH₃—(CH₂)₂— >245 β I-1-a-20 CH₃ CH₃ 4-Cl H H—CH₂—CHCH₃—(CH₂)₃— >245 β I-1-a-21 CH₃ CH₃ 4-Cl H —(CH₂)₄— H >240 —I-1-a-22 CH₃ CH₃ 4-Cl H i-C₃H₇ H H >249 — I-1-a-23 CH₃ CH₃ 2-CH₃ 5-CH₃ H—CH₂—O—(CH₂)₃— 148 — I-1-a-24 CH₃ CH₃ 2-CH₃ 6-CH₃ H —CH₂O—(CH₂)₃— >250 —I-1-a-25 CH₃ CH₃ 3-CH₃ 5-CH₃ H —CH₂—O—(CH₂)₃— >250 — I-1-a-26 CH₃ Cl4-Cl H H —(CH₂)₅— >250 — I-1-a-27 CH₃ Cl 3-CF₃ 5-CF₃ H —(CH₂)₅— >250 —I-1-a-28 CH₃ Cl 4-CF₃ H H —(CH₂)₅— >250 — I-1-a-29 CH₃ Cl 2-Cl 4-Cl H—(CH₂)₅— >250 — I-1-a-30 CH₃ Cl 3-Cl 5-Cl H —(CH₂)₅— >250 — I-1-a-31C₂H₅ C₂H₅ 4-Cl H H —(CH₂)₂—CHCH₃—(CH₂)₂— >250 — I-1-a-32 C₂H₅ C₂H₅ 3-CF₃5-CF₃ H —(CH₂)₂CHCH₃—(CH₂)₂— 242-244 β I-1-a-33 C₂H₅ C₂H₅ 4-CF₃ H H—(CH₂)₂CHCH₃—(CH₂)₂— >250 β I-1-a-34 CH₃ CH₃ 4-Cl H H i-C₃H₇ CH₃ Wax —I-1-a-35 C₂H₅ C₂h₅ 2-Cl 4-Cl H —(CH₂)₂CHCH₃—(CH₂)₂— >250 β I-1-a-36 C₂H₅C₂H₅ 3-Cl 5-Cl H —(CH₂)₂CHCH₃—(CH₂)₂— >250 β I-1-a-37 CH₃ CH₃ 2-Cl 4-ClH i-C₃H₇ CH₃ 115-117 — I-1-a-38 CH₃ CH₃ 3-Cl 5-Cl H i-C₃H₇ CH₃ 233-234 —I-1-a-39 C₂H₅ Cl 4-Cl H H CH₃ CH₃ >250 — I-1-a-40 C₂H₅ Cl 3-Cl 5-Cl HCH₃ CH₃ 125-127 — I-1-a-41 CH₃ Cl 4-Cl H H CH₃ CH₃ >250 — I-1-a-42 CH₃Cl 3-CF₃ 5-CF₃ H CH₃ CH₃ >250 — I-1-a-43 CH₃ CH₃ 4-Cl H H i-C₃H₇CH₃ >250 — I-1-a-44 CH₃ CH₃ 4-CH₃ H H —(CH₂)₂—CHOCH₃—(CH₂)₂— >235 βI-1-a-45 CH₃ CH₃ 2-CH₃ 5-F H —(CH₂)₂—CHOCH₃—(CH₂)₂— >235 β I-1-a-46 CH₃CH₃ 2-CH₃ 5-CH₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— 168 β I-1-a-47 CH₃ CH₃ 2-OCH₃ HH —(CH₂)₂—CHOCH₃—(CH₂)₂— β I-1-a-48 CH₃ CH₃ 3-CH₃ 5-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— 238 β I-1-a-49 CH₃ CH₃ 2-Cl 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— 188 β I-1-a-50 CH₃ CH₃ 2-Cl 3-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— >235 β

EXAMPLE I-1-b-1

[1112]

[1113] First 0.67 ml (4.8 mmol) of triethylamine and then, at refluxtemperature, 0.5 ml (0.005 mol) of isobutyryl chloride in 5 ml ofabsolute ethyl acetate are added to 1.58 g of the compound of ExampleI-1-a-19 in 40 ml of absolute ethyl acetate.

[1114] Stirring is continued at this temperature until the reaction hasended (monitored by thin-layer chromatography). The mixture is thenconcentrated and the residue is taken up in methylene chloride, washedtwice with 30 ml of 0.5 N NaOH, dried and concentrated. The residue isrecrystallized from methyl tert-butyl ether (MTBE)/n-hexane. Yield 1.27g (68 % of theory). m.p.: >247° C.

[1115] By the method of Example (I-1-b-1), and/or in accordance with thegeneral procedures for preparing compounds of the formula (I-1-b), thefollowing compounds of the formula (I-1-b) are obtained: (I-1-b)

Ex. No. X Z V¹ V² D A B R¹ m.p. ° C. isomer I-1-b-2 CH₃ CH₃ 4-Cl H H—(CH₂)₂—CHCH₃—(CH₂)₂— H₅C₂—O—CH₂— >247 β I-1-b-3 CH₃ CH₃ 4-Cl H H—CH₂—CHCH₃—(CH₂)₃— i-C₃H₇— >247 β I-1-b-4 CH₃ CH₃ 4-Cl H H—CH₂—CHCH₃—(CH₂)₃—

>254 β I-1-b-5 CH₃ CH₃ 4-Cl H H —CH₂—CHOCH₃—(CH₂)₂— i-C₃H₇— 236 βI-1-b-6 CH₃ CH₃ 4-Cl H H —CH₂—CHOCH₃—(CH₂)₂—

>247 β I-1-b-7 CH₃ CH₃ 3-Cl H H —CH₂—CHOCH₃—(CH₂)₂— i-C₃H₇— 238 β

EXAMPLE I-1-c-1

[1116]

[1117] At −10° C. to 0° C., 0.15 g of chloroformic acid in 5 ml ofmethylene chloride is added to 0.35 g of the compound of ExampleI-1-a-12 and 0.15 ml of triethylamine in 30 ml of methylene chloride,and the mixture is stirred at room temperature for 2 hours. The reactionmixture is filtered through silica gel using methylene chloride/ethylacetate 5:3 as mobile phase, and is then concentrated and dissolved in alittle methylene chloride, and the product is precipitated out byaddition of hexane.

[1118] Yield 0.23 g (56 % of theory). m.p.: 129° C.

[1119] By the method of Example (I-1-c-1), and/or according to thegeneral procedures for preparing compounds of the formula (I-1-c), thefollowing compounds of the formula (I-1-c) are obtained: (I-1-c)

Ex.- m.p. No. X Z V¹ V² D A B L M R² ° C. isomer I-1-c-2 CH₃ CH₃ 4-Cl HH —(CH₂)₂—CHCH₃—(CH₂)₂— O O C₂H₅— >240 β I-1-c-3 CH₃ CH₃ 4-Cl H H—CH₂—CHCH₃—(CH₂)₃— O O C₂H₅— >240 β I-1-c-4 CH₃ CH₃ 4-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— O O C₂H₅— 202 β I-1-c-5 CH₃ CH₃ 3-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— O O C₂H₅— 214 β I-1-c-6 CH₃ CH₃ 3-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— O O

248 β I-1-c-7 CH₃ CH₃ 3-Cl H H —(CH₂)₂—CHOCH₃—(CH₂)₂— O O

239 β

EXAMPLE I-2-a-1

[1120]

[1121] 1.0 g (2.6 mmol) of3-[(2,6-dimethyl4-bromo)-phenyl]-5,5-[(3-methoxy)-pentamethylene]-4-hydroxy-Δ³-dihydrofuran-2-oneaccording to Example I-2-a-15 from WO 97/02243 is suspended in 20 ml ofdiethoxyethane, 0.5 g (3.2 mmol) of 4-chlorophenylboronic acid and 180mg (0.156 mmol) of tetrakis(triphenylphosphine)palladium are added andthe mixture is stirred at room temperature for 15 minutes, after which13 ml of 20% strength sodium carbonate solution are added, and stirringis continued at 80° C. for 24 h.

[1122] For work-up, the mixture was concentrated, partitioned betweenaqueous citric acid and methylene chloride, dried and concentrated. Forfurther purification, the crude product was partitioned between 1N NaOHand methylene chloride, the aqueous phase was acidified and theprecipitated product was filtered off with suction and dried.

[1123] Yield: 0.38 g (35% of theory) of a crystalline solid m.p.:215-217° C.

EXAMPLE I-2-a-5

[1124]

[1125] 9.4 ml of 1 M solution of potassium tert-butoxide in DMF areslowly added dropwise to 7.82 mmol of the compound of Example (III-1) in10 ml of DMF, and the mixture is stirred at room temperature overnight.The solvent is distilled off, the residue is taken up in water andacidified with dilute hydrochloric acid. The mixture is stirred foranother 2 hours and then filtered off with suction.

[1126] Yield: 2.78 g, m.p. 285-287° C.

[1127] By the method of Example (I-2-a-1) and (I-2-a-5), and inaccordance with the general procedures for preparing compounds of theformula (I-2-a) the following compounds of the formula (I-2-a) areobtained: (I-2-a)

Ex. No. X Z V¹ V² A B m.p. ° C. I-2-a-2 Cl H 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— 223-225 I-2-a-3 CH₃ Cl 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— 157-160 I-2-a-4 C₂H₅ CH₃ 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— 212-215 I-2-a-5 CH₃ CH₃ 4-Cl H CH₃ CH₃ 285-287I-2-a-6 CH₃ CH₃ 4-Cl H —(CH₂)₄— 263-266 I-2-a-7 CH₃ CH₃ 4-Cl H —(CH₂)₅—242-244 I-2-a-8 CH₃ CH₃ 4-Cl H —CH₂—CHCH₃—(CH₂)₃— 221-223 I-2-a-9 CH₃CH₃ 4-Cl H —(CH₂)₂—CHCH₃—(CH₂)₂— 249-251 I-2-a-10 CH₃ CH₃ 4-Cl H—CH₂—O—(CH₂)₃— 255-258 I-2-a-11 CH₃ CH₃ 4-Cl H —(CH₂)₂—O—(CH₂)₂— 274-276I-2-a-12 CH₃ CH₃ 4-Cl H —CH₂—CHCH₃—O—(CH₂)₂— 168-170 I-2-a-13 CH₃ CH₃4-Cl H —(CH₂)₂—CHOC₂H₅(CH₂)₂ 214-217 I-2-a-14 CH₃ CH₃ 4-Cl H

225-228

EXAMPLE I-2-b-1

[1128]

[1129] 0.32 g of triethylamine and then 0.33 g of isobutyryl chlorideare added to 1.03 g of the compound of Example 1-2-a-5 in 20 ml ofmethylene chloride. The mixture is stirred overnight and then shakenwith dilute aqueous citric acid and 1 N NaOH, and the organic phase isdried and concentrated. Yield 1.16 g.

[1130]¹H NMR (CDCl₃): 1.05 ppm (d, 6H); 1.55 ppm (s, 6H); 2.25 ppm (s,6H); 2.65 ppm (m, 1H), 7.25-7.50 ppm (m, 6H).

[1131] By the method of Example (I-2-b-1), and/or in accordance with thegeneral procedures for preparing compounds of the formula (I-2-b) thefollowing compounds of the formula (I-2-b) are obtained: (I-2-b)

m.p. Ex. No. X Z V¹ V² A B R¹ ° C. I-2-b-2 CH₃ CH₃ 4-Cl H —(CH₂)₄—i-C₃H₇— oil I-2-b-3 CH₃ CH₃ 4-Cl H —(CH₂)₅— i-C₃H₇— oil I-2-b-4 CH₃ CH₃4-Cl H —CH₂—CHCH₃—(CH₂)₃— i-C₃H₇— oil I-2-b-5 CH₃ CH₃ 4-Cl H—(CH₂)₂—CHCH₃—(CH₂)₂— i-C₃H₇— oil I-2-b-6 CH₃ CH₃ 4-Cl H —CH₂—O—(CH₂)₃—i-C₃H₇— oil I-2-b-7 CH₃ CH₃ 4-Cl H —(CH₂)₂—O—(CH₂)₂— i-C₃H₇— oil I-2-b-8CH₃ CH₃ 4-Cl H —CH₂—CHCH₃—O—(CH₂)₂— i-C₃H₇— oil I-2-b-9 CH₃ CH₃ 4-Cl H—(CH₂)₂—CHOC₂H₅—(CH₂)₂— i-C₃H₇— oil

EXAMPLE I-2-c-1

[1132]

[1133] By the method of Example (I-2-b-1), the compound shown above isobtained starting from the compound of Example (I-2-a-13) and isopropylchloroformate.

EXAMPLE I-3-a-1

[1134]

[1135] 45.0 g (81 mmol) of the compound of Example (IV-1) in 91 ml oftrifluoroacetic acid and 210 ml of toluene are heated at refluxovernight. The mixture is concentrated and the residue is then taken upin 200 ml of MTBE and 600 ml of water and adjusted to pH 14 by additionof NaOH. The organic phase is added dropwise to 11 of 1N HCl, themixture is stirred for 2 hours, the product is filtered off withsuction, washed with cyclohexane and dried. Yield 18.3 g (57 % oftheory) m.p.: >250° C.

EXAMPLE I-3-b-1

[1136]

[1137] With ice-cooling, a solution of 0.79 ml of isovaleryl chloride in3 ml of absolute methylene chloride is added dropwise to 2.0 g of thecompound of Example (I-3-a-1) and 1.04 ml of triethylamine in 15 ml ofabsolute methylene chloride, and the mixture is stirred at roomtemperature for 2 hours. The mixture is washed with 10% strength aqueouscitric acid and extracted with methylene chloride. The organic phase iswashed with 1N NaOH, dried and concentrated. Yield 2.1 g (87 % oftheory) of an oil.

[1138]¹H NMR (400 MHz, CDCl₃): δ=0.9/(dd, 6 H, CH/CH₃)₂, 1.4-2.0 (m,10H, cyclohexyl) 2.15 (s, 6H, 2×Ar—CH₃), 7.4 -7.7 (m, 6H, Ar—H) ppm.

EXAMPLE I-3-c-1

[1139]

[1140] By the method of Example (I-3-b-1) the compound shown above isobtained by reacting the compound of Example (I-3-a-1) with ethylchloroformate. Yield 2.1 g (89% of theory). m.p. 167 to 170° C.

EXAMPLE (I-5-a-1)

[1141]

[1142] 1.8 g of 4-chlorophenylboronic acid and 266.3 mg ofbis(triphenylphosphine)-palladium(II) chloride are added to 2.6 g of thecompound of Example (1-5-a-1) from WO 97/02 243 in 21 ml ofdimethoxyethane and 18 ml of 1N Na₂CO₃ solution. The mixture is stirredat reflux overnight, acidified with dilute HCl and concentrated. Theresidue is purified by silica gel chromatography (mobile phasecyclohexane/ethyl acetate 4/1→2/1). Yield 2.55 g (89% of theory);m.p.: >250° C.

EXAMPLE (I-5-a-2)

[1143]

[1144] By the method of Example I-5-a-1, the compound shown above isobtained starting from the compound of Example (I-5-a-6) from WO 97102243. m.p. 107-108° C.

EXAMPLE I-7-a-1

[1145]

[1146] 1.5 g (4.3 mmol) of the compound of the formula

[1147] are dissolved in 10 ml of dimethoxyethane and admixed with 10 mlof 1 M Na₂CO₃ solution. 1.0 g (6.45 mmol) of p-chlorophenylboronic acidand finally, as catalyst, 254 mg (0.22 mmol) of Pd(PPh₃)₄ (Ph=phenyl)are added. The mixture is heated at reflux overnight and then filtered,and the filter cake is rinsed with ethyl acetate. The filtrate isadmixed with water and extracted 3 times each with ethyl acetate andmethyl tert-butyl ether (MTBE). The combined organic phases are washedwith water and saturated NaCl solution, dried and concentrated.

[1148] Crude yield: 1.85 g.

[1149] Silica gel column chromatography using cyclohexane/ethyl acetate15/1 gives 100 mg of the compound shown above.

[1150] Two other fractions (300 mg and 400 mg) of rotamers of the cisisomer are obtained.

EXAMPLE I-7-a-2

[1151]

[1152] 20.5 g of the compound of Example (X-1) in 50 ml of absolute DMFare admixed with 8.44 g of potassium tert-butoxide and heated at 80° C.for 1 hour. With ice-cooling, the mixture is slowly added to 21 of 1NHCl. The mixture is extracted with methylene chloride and the extract isdried and concentrated. Yield 18 g (95% of theory), m.p.: 192-195° C.

[1153] By the method of Example (I-7-a-1) and (I-7-a-2), and/or inaccordance with the general procedures for preparing compounds of theformula (I-7-a) the following compounds of the formula (I-7-a) areobtained:

Ex.- m.p. No. X Z V¹ V² B A Q¹ Q² ° C. I-7-a-3 CH₃ CH₃ 3-Cl H —(CH₂)₅ HH >250 I-7-a-4 CH₃ CH₃ 4-Cl H H —(CH₂)₄— H >250 I-7-a-5 CH₃ CH₃ 3-Cl H H—(CH₂)₄— H 211- 213 I-7-a-6 CH₃ CH₃ 4-Cl H —(CH₂)₃—CHCH₃—CH₂— H H 243-244 I-7-a-7 CH₃ CH₃ 3-Cl H —(CH₂)₃—CHCH₃—CH₂— H H wax

EXAMPLE I-7-b-1

[1154]

[1155] By the method of Example (I-3-b-1), the compound shown above isobtained by reacting the compound of Example (I-7-a-1) with isobutyrylchloride. m.p.: oil.

[1156]¹H NMR (400 MHz; DMSO): δ=0.9-1.0 (d, 6H, HC—CH ₃); 1.2-2.0 (m,8H, cyclohexyl-H); 2.1 2.15 (s, 6H, 2×ArCH₃); 2.65 (m, 1H, CHCH₃); 7.4(s, 2H, Ar—H); 7.5-7.7 (d, 4H, Ar—H) ppm.

EXAMPLE I-7-b-2

[1157]

[1158] By the method of Example (I-3-b-1) the compound shown above isobtained as an oil by reacting the compound of Example (I-7-a-5) withisobutyryl chloride.

[1159]¹H NMR (400 MHz; DMSO): δ=1-1.1 (d, 6H, CH—CH ₃), 42.0 (m, 8H,cyclohexyl-H); 2.15-2.2 (s, 6H, 2×ArCH₃); 2.6 (m, 1H, CH—CH₃); 2.9-3.4(m, 2H, cyclohexyl C—H); 7.3-7.6 (m, 6H, Ar—H) ppm.

[1160] By the method of Example (I-7-b-1), and/or in accordance with thegeneral procedures for preparing compounds of the formula (I-7-b), thefollowing compounds of the formula (I-7-b) are obtained:

Ex. No. X Z V¹ V² B A Q¹ Q² R¹ m.p. ° C. I-7-b-3 CH₃ CH₃ 4-Cl H —(CH₂)₅—H H i-C₄H₉ oil

EXAMPLE I-7-c-1

[1161]

[1162] By the method of Example (I-3-b-1), the compound shown above isobtained as a wax by reacting the compound of Example (I-7-a-2) withethyl chloroformate.

EXAMPLE I-8-a-1

[1163]

[1164] 6.0 g of the compound of Example (XI-1) are initially charged in20 ml of DMF, admixed with 2.63 g of potassium tert-butoxide and heatedat 80° C. for 1 hour. With ice-cooling, the mixture is then slowly addedto 11 of 1N HCl, and the product is filtered off with suction and dried.Yield 5.15 g (93% of theory). m.p.: 222-224° C.

EXAMPLE I-8-a-2

[1165] By the method of Example (I-8-a-1),

[1166] of m.p. 117-122° C. is obtained.

EXAMPLE I-8-b-1

[1167]

[1168] By the method of Example (I-3-b-1), the compound shown above isobtained as an oil by reacting the compound of Example (I-8-a-1) andisovaleryl chloride.

[1169]¹H NMR (400 MHz; CDCl₃): δ=0.55 (d, 6H, CH(CH ₃)₂), 1.2 (s, 6H,C(CH ₃)₂), 1.6 (m, 1H, CH(CH₃)₂), 2.1 (s, 6H, 2×Ar—CH₃), 7.3-7.65 (m,6H, Ar—H) ppm.

EXAMPLE I-8-b-2

[1170]

[1171] By the method of Example (I-3-b-1), the compound shown above isobtained as an oil by reacting the compound of Example (I-8-a-2) withisovaleryl chloride.

[1172] 1H NMR (400 MHz; CDCl₃): δ=0.55 (d, 6H, CH(CH ₃)₂), 1.2 (s, 6H,C(CH ₃)₂), 1.6 (m, 1H, CH(CH₃)₂), 2.0;2.7 (t, 2×2H, CH ₂—CH ₂), 2.05 (s,6H, 2×Ar—CH₃), 7.3-7.65 (m, 6H, Ar—H) ppm.

EXAMPLE I-8-c-1

[1173]

[1174] By the method of Example (I-3-b-1), the compound shown above isobtained as a wax-like substance by reacting the compound of Example(I-8-a-1) with ethyl chloroformate.

[1175]¹H NMR (400 MHz; CDCl₃): δ=1.05 (t, 3H, CH₂CH ₃, 1.2 (s, 6H,C(CH₃)₂), 2.1 (s, 6H, 2×Ar—CH₃), 2.45;2.7 (s, 2×2H, CH₂), 4.1 (q, 2H, CH₂—CH3) 7.35-7.7 (m, 6H, Ar—H) ppm.

EXAMPLE I-8-c-2

[1176]

[1177] By the method of Example 1-3-b-1, the compound shown above isobtained as a wax-like substance by reacting the compound of Example(I-8-a-2) with ethyl chloroformate.

[1178]¹H NMR (400 MHz; CDCl₃): δ=1.05 (t, 3H, CH₂CH ₃, 1.15 (s, 6H,C(CH₃)₂), 2.0; 2.7 (t, 2×2H, CH ₂—CH₂) 2.05 (s, 6H, Qx, Ar—CH₃), 4.05(q, 2H, CH ₂—CH3) 7.3-7.7 (m, 6H, Ar—H) ppm.

EXAMPLE II-1

[1179]

[1180] At a temperature of from 30 to 40° C., 7.75 g of the compound ofExample XXIX-1 in 80 ml of methylene chloride are added dropwise to 10.3g of concentrated sulphuric acid, and the mixture is stirred at thistemperature for 2 hours. 14 ml of methanol are then added dropwise, andthe mixture is stirred at 70° C. for a further 6 hours. The mixture isthen poured onto 110 g of ice and extracted with methylene chloride, andthe organic phase is washed with aqueous NaHCO, solution, dried andconcentrated. The residue is recrystallized from MTBE/n-hexane and thenpurified farther by silica gel column chromatography (mobile phasemethylene chloride/ethyl acetate 5/3).

[1181] Yield 4.24 g (50% of theory). m.p.: 142° C.

EXAMPLE 11-2

[1182]

[1183] At 5-10° C., 5.86 g of2,6-dimethyl-4-(4-chlorophenyl)-phenylacetyl chloride according toExample (XXIV-1) in 10 ml of acetonitrile are added dropwise to 4.57 gof methyl 3-methyl-1-amino-cyclohexane carboxylate x hydrochloride and10 g of ground K₂CO₃ in 20 ml of acetonitrile, and the mixture isstirred at room temperature for 3 hours. The mixture is poured into 200ml of ice-water and filtered off with suction, and the residue is takenup in methylene chloride, dried and concentrated. The residue isrecrystallized from MTBE/n-hexane. Yield 7.12 g (83% of theory), m.p.:169° C.

[1184] By the method of Examples (11-1) and (II-2), and/or in accordancewith the general procedures for preparing compounds of the formula (II),the following compounds of the formula (11) are obtained: (II)

Ex.- m.p. iso- No. X Z V¹ V² D A B R⁸ ° C. mer II-3 CH₃ CH₃ 3-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 88 β II-4 CH₃ CH₃ 4-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 127 β II-5 CH₃ CH₃ 2-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 75 β II-6 CH₃ CH₃ 4-Cl H H —(CH₂)₂—O—(CH₂)₂—CH₃ 179 — II-7 CH₃ CH₃ 4-Cl H H —(CH₂)₂—OCHC₂H₅—(CH₂)₂— CH₃ 146 β II-8CH₃ CH₃ 4-Cl H H —(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 167 β II-9 CH₃ CH₃ 4-CH₃ H H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 159 β II-10 CH₃ CH₃ 2-CH₃ 5-F H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 138 β II-11 CH₃ CH₃ 2-CH₃ 5-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 71 β II-12 CH₃ CH₃ 2-CH₃ 3-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 133 β II-13 CH₃ CH₃ 2-OCH₃ H H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 156 β II-14 CH₃ CH₃ 3-CH₃ 5-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 169 β II-15 CH₃ CH₃ 2-Cl 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 125 β II-16 CH₃ CH₃ 2-Cl 3-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 127 β II-17 CH₃ CH₃ 4-Cl H —(CH₂)₄— H C₂H₅oil — II-18 CH₃ CH₃ 4-Cl H —(CH₂)₂—S—CH₂— H C₂H₅ 81 — II-19 CH₃ CH₃ 4-ClH i-C₃H₇ H H C₂H₅ 119 —

EXAMPLE XXIX-1

[1185]

[1186] At 5-10° C., 8.79 g of2,6-dimethyl-4-(4-chlorophenyl)-phenylacetyl chloride in 15 ml ofacetonitrile are added dropwise to 3.7 g of2-amino-2,3-dimethyl-butyronitrile and 13.8 g of ground K₂CO₃ in 30 mlof acetonitrile, and the mixture is stirred at room temperature for 3hours. The mixture is poured into 250 ml of ice-water and filtered offwith suction, and the residue is washed with water. The residue is takenup in methylene chloride, and the solution is dried and concentrated.The product is subsequently purified by silica gel chromatography(mobile phase n-hexane/ethyl acetate 3/1). Yield 8.24 g (74% of theory),m.p. 180° C.

EXAMPLE (III-1)

[1187]

[1188] The mixture of 2.29 g of the compound of Example (XXIV-1) and1.03 g of ethyl hydroxyisobutyrate is heated at 1 40° C overnight.

[1189] GC/MS: m/e =115 (8 %), 179 (34 %), 229 (100 %), 256 (12 %), 388(20 %).

[1190] By the method of Example (III-1), and/or in accordance with thegeneral procedures for preparing compounds of the formula. (III), thefollowing compounds of the formula (III) are obtained: (III)

Ex. m.p. No. X Z V¹ V² A B R⁸ ° C. III-2 CH₃ CH₃ 4-Cl H —(CH₂)₄— C₂H₅oil* III-3 CH₃ CH₃ 4-Cl H —(CH₂)_(5—) C₂H₅ oil* III-4 CH₃ CH₃ 4-Cl H—CH₂—CHCH₃—(CH₂)₃— C₂H₅ oil* III-5 CH₃ CH₃ 4-Cl H —(CH₂)₂—CHCH₂—(CH₂)₂—C₂H₅ oil* III-6 CH₃ CH₃ 4-Cl H —CH₂—O—(CH₂)₃— C₂H₅ oil* III-7 CH₃ CH₃4-Cl H —(CH₂)₂—O—(CH₂)₂— C₂H₅ oil* III-8 CH₃ CH₃ 4-Cl H—CH₂—CHCH₃—O—(CH₂)₂— C₂H₅ oil* III-9 CH₃ CH₃ 4-Cl H—(CH₂)₂—CHOC₂H₅—(CH₂)₂— C₂H₅ oil* III-10 CH₃ CH₃ 4-Cl H

C₂H₅ oil*

EXAMPLE (IV-1)

[1191]

[1192] A: 15.0 g of the compound,

[1193] 9.63 g of thionyl chloride and 1 drop of DMF were stirred at roomtemperature for 5 minutes and then at 100° C. until the evolution of gashad ceased. The mixture is then concentrated and dried under highvacuum.

[1194] B: At 0° C., 25.3 g of the compound of Example (XXXII-1) areadded dropwise to 45.8 ml (96.3 mmol) of a lithium diisopropylamide(LDA) solution in 100 ml of absolute tetrahydrofuran (THF), and themixture is stirred at this temperature for 30 minutes. The acyl chlorideobtained according to A is then added dropwise in 30 ml of THF, coolingis removed and the mixture is stirred for another hour. 300 ml of MTBEand a few drops of water are added and the mixture is washed twice with300 ml of 10% aqueous ammonium chloride solution each time, dried andconcentrated. Yield 45 g (100% of theory) as an oil.

[1195]¹H NMR (CDCl₃, 400 MHz): δ=1.5-2.0 (m, 10H, cyclohexyl), 2.4 (s,6H, 2×Ar—CH₃), 3.1; 3.3 (d, 2H, S—CH ₂) 3.6; 3.7 (s, 2×3H, 2×OCH₃),6.8-7.7 (m, 10H, Ar—H) ppm.

EXAMPLE X-1

[1196]

[1197] 70.0 g of the compound of Example (XXXVIII-1), 24.05 g ofpotassium carbonate and 74.4 g of methyl iodide in 400 ml of acetone arestirred under reflux for 16 hours. The mixture is filtered and thefiltrate is concentrated. The residue is chromatographed over silica gel(mobile phase methylene chloride/petroleum ether 4/1). Yield 20.5 g (41%of theory) of an oil.

[1198]¹H NMR (CDCl₃, 400 MHz): δ=1.3-1.8 (m, 10 H, cyclohexyl), 2.2 (s,6H, 2×Ar—CH ₃), 2.95 (s, 2H, CH₂CO), 3.55 (s, 3H, OCH₃), 3.85 (s, 2H,Ar—CH₂), 7.3 -7.65 (m, 6H, Ar—H) ppm.

EXAMPLE (XXXVIII-1)

[1199]

[1200] At −15° C., a solution of 51.9 g of the compound of Example(XXII-1) in 80 ml of THF is added dropwise to 100 ml of a solution ofLDA (2 molar) and 200 ml of THF, and the mixture is subsequently stirredat 0° C. for 1 hour. At −15° C., a solution of 20.2 g of the compound

[1201] in 30 ml of THF is then added dropwise. The mixture is stirred atroom temperature for 2 hours, 300 ml of water and 80 g of ammoniumchloride are added and the mixture is acidified with concentrated HCR.The mixture is extracted with ether and the ether phase is concentrated.The residue is boiled under reflux with 200 g of KOH and 660 ml of waterfor 2 days. After cooling, the mixture is acidified with concentratedHCl and extracted with ether. The crude oily product which remains afterconcentration is reacted further without any further purification. Yield70 g (100% of theory).

EXAMPLE (XI-1)

[1202]

[1203] 36 g of the compound of Example (XLII-1), 13.2 g of potassiumcarbonate and 40.8 g of methyl iodide in 200 ml of acetone are boiledunder reflux for 16 hours. The mixture is filtered, the filtrate isconcentrated and the residue is purified by silica gel columnchromatography (mobile phase methylene chloride/petroleum ether 2/1).

[1204] Yield 12 g (52% of theory), oil.

[1205]¹H NMR (400 MHz, CDCl₃,): δ=1.05 (s, 6H, C(CH₃)₂, 2.2 (s, 6H,2×Ar—CH ₃), 2.4; 2.7 (s, 2×2H, CO—CH ₂), 3.6 (s, 3H, OCH₃), 3.85 (s, 2H,Ar—CH₂), 7.3-7.65 (m, 6H, Ar—H) ppm.

EXAMPLE (XI-2)

[1206]

[1207] By the method of Example (XI-1), the compound shown above isobtained, likewise as an oil.

[1208]¹H NMR (400 MHz, CDCl₃,): δ=1.1 (s, 6H, C(CH ₃)₂), 1.75; 2.55 (t,2×2H, CH₂CH₂), 2.2 (s, 6H, 2×Ar—CH₃), 3.6 (s, 3H, OCH₃), 3.9 (s, 2H,ArCH₂, 7.3-7.7 (m, 6H, Ar—H) ppm.

EXAMPLE (XLII-1)

[1209]

[1210] At −15° C., a solution of 27 g of the compound of Example(XXXII-1) in 30 ml of THF is added dropwise to 50 ml of a solution ofLDA (2 molar) in 100 ml of THF, and the mixture is stirred at 0° C. for1 hour. At −15° C., a solution of 8.6 g of the compound

[1211] in 20 ml of THF is then added dropwise. The mixture is stirred atroom temperature for 2 hours, after which 150 ml of water and 40 g ofammonium chloride are added, and the mixture is acidified withconcentrated HCl. The mixture is extracted with ether and the etherphase is concentrated. The residue is boiled under reflux with 100 g ofKOH and 330 ml of water for 2 days. After cooling, the mixture isacidified with concentrated HCl and extracted with ether. The crudeproduct (36 g) which remains after concentration is reacted furtherwithout any further purification.

EXAMPLE (LXII-2)

[1212]

[1213] By the method of Example (LXII-1), the compound shown above isobtained.

EXAMPLE XXIV-1

[1214]

[1215] 69 g of the acid of Example XXVII-1 are heated with 55 ml ofthionyl chloride at 70° C. until the evolution of gas has ceased.

[1216] Excess thionyl chloride is subsequently removed under reducedpressure. Yield 54.9 g (74% of theory), m.p.: 102° C.

[1217] By the method of Example (XXIV-1), and/or in accordance with thegeneral procedures for preparing the compounds of the formula (XXIV),the following compounds of the formula (XXIV) are obtained: (XXIV)

Ex. No. X Z V¹ V² m.p. ° C. XXIV-2 CH₃ CH₃ 3-Cl H * XXIV-3 CH₃ CH₃ 2-ClH * XXIV-4 CH₃ CH₃ 4-CH₃ H * XXIV-5 CH₃ CH₃ 2-CH₃ 5-F * XXIV-6 CH₃ CH₃2-CH₃ 5-CH₃ * XXIV-7 CH₃ CH₃ 2-CH₃ 3-CH₃ * XXIV-8 CH₃ CH₃ 2-OCH₃ H *XXIV-9 CH₃ CH₃ 3-CH₃ 5-CH₃ * XXIV-10 CH₃ CH₃ 2-Cl 4-Cl * XXIV-11 CH₃ CH₃2-Cl 3-Cl *

EXAMPLE MXVII-1)

[1218]

[1219] At room temperature, 6 g of the compound of Example (XXXII-1),1.2 g of lithium hydroxide, 20 ml of ethanol, 100 ml of water and 100 mlof THF are stirred over-night. The THF is removed under reduced pressureand the aqueous solution that remains is repeatedly extracted withmethylene chloride. The aqueous phase is acidified with concentrated HCland the precipitated product is filtered off with suction. Yield 5 g(96% of theory), m.p. 205° C.

[1220] By the method of Example (XXVII-1), and/or in accordance with thegeneral procedures for preparing the compounds (XXVII), the followingcompounds of the formula (XXVII) are obtained: (XXVII)

Ex. No. X Z V¹ V² m.p. ° C. XXVII-2 CH₃ CH₃ 3-Cl H 143 XXVII-3 CH₃ CH₃2-Cl H 129 XXVII-4 CH₃ CH₃ 4-CH₃ H 154 XXVII-5 CH₃ CH₃ 2-CH₃ 5-F 120XXVII-6 CH₃ CH₃ 2-CH₃ 5-CH₃ 141 XXVII-7 CH₃ CH₃ 2-CH₃ 3-CH₃ 155 XXVII-8CH₃ CH₃ 2-OCH₃ H 151 XXVII-9 CH₃ CH₃ 3-CH₃ 5-CH₃ 173 XXVII-10 CH₃ CH₃2-Cl 4-Cl 166 XXVII-11 CH₃ CH₃ 2-Cl 3-Cl 158

EXAMPLE (XXXII-1)

[1221]

[1222] 30 g of the compound of Example (XLV-1) are boiled under refluxwith 19.8 g of 88% strength KOH in 1000 ml of methanol overnight. Aftercooling, the mixture is admixed with 20 ml of concentrated sulphuricacid and boiled under reflux for 1 hour. The solid is filtered off withsuction and washed with methanol. The methanol in the filtrate isremoved under reduced pressure, and the residue is admixed with waterand extracted with methylene chloride. The organic phase is dried andconcentrated. Yield 1 g (10% of theory), oil.

[1223]¹H NMR (400 MHz, CDCl₃,): δ=2.38 (s, 6H, Ar—CH ₃), 3.70 (s, 3H,OCH ₃), 3.73 (s, 2H, CH ₂), 7.23 (s, 2H ArH), 7.36-7.39 (AA′, BB′, 2H,ArH), 7.48-7.51 (AA′, BB′, 2H, Ar—H) ppm.

EXAMPLE (XXXII-2)

[1224]

[1225] Under argon, 6.1 g of 3-chlorophenylboronic acid, 0.15 g ofbis(triphenylphosphine)palladium(II) chloride and 65 ml of 1M Na₂CO₃solution are introduced into 7.68 g of methyl 4-bromo-2,6-dimethylphenylacetate in 85 ml of dimethoxyethane, and the mixture is stirred underreflux overnight. The mixture is diluted with water and extracted withethyl acetate. The organic phase is washed with ammonium chloridesolution, water and saturated sodium chloride solution, dried andconcentrated. Yield 4.3 g (36% of theory), m.p.: 56° C.

[1226] By the method of Examples (XXII-1) and (XXXII-2), and/or inaccordance with the general procedures for preparing the compounds(XXXII), the following compounds of the formula (XXXII) are obtained:(XXXII)

Ex. No. X Z V¹ V² R⁸ m.p. ° C. XXXII-2 CH₃ CH₃ 3-Cl H CH₃ 56 XXXII-3 CH₃CH₃ 2-Cl H CH₃ oil XXXII-4 CH₃ CH₃ 4-CH₃ H CH₃ 137  XXXII-5 CH₃ CH₃2-CH₃ 5-F CH₃ oil XXXII-6 CH₃ CH₃ 2-CH₃ 5-CH₃ CH₃ oil XXXII-7 CH₃ CH₃2-CH₃ 3-CH₃ CH₃ oil XXXII-8 CH₃ CH₃ 2-OCH₃ H CH₃ 85 XXXII-9 CH₃ CH₃3-CH₃ 5-CH₃ CH₃ oil XXXII-10 CH₃ CH₃ 2-Cl 4-Cl CH₃ oil XXXII-11 CH₃ CH₃2-Cl 3-Cl CH₃ oil

EXAMPLE XLVI-1

[1227]

[1228] 5 g of 4-bromo-2,6-dimethylaniline, 3.88 g of4-chlorophenylboronic acid and 0.11 g ofbis(triphenylphosphine)palladium(II) chloride in 48.8 ml of 1M Na₂CO₃solution and 65 ml of dimethoxyethane are heated under reflux overnight.The mixture is admixed with water and extracted with ethyl acetate. Theorganic phase is washed with ammonium chloride solution, water andsaturated sodium chloride solution, dried and concentrated. Yield 4 g(77% of theory), m.p.: 96° C.

1. Compounds of the formula (I)

in which X represents halogen, alkyl, alkoxy, alkenyloxy, alkylthio,alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkoxy,halogenoalkenyloxy, nitro, cyano or in each case optionally substitutedphenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio, Yrepresents in each case optionally substituted cycloalkyl, aryl orhetaryl, Z represents hydrogen, halogen, alkyl, alkoxy, alkenyloxy,halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano, CKErepresents one of the groups

 in which A represents hydrogen, in each case optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl,alkylthioalkyl, saturated or unsaturated, optionally substitutedcycloalkyl in which optionally at least one ring atom is replaced by aheteroatom, or in each case optionally halogen-, alkyl-, halogenoalkyl-,alkoxy-, halogenoalkoxy-, cyano- or nitro-substituted aryl, arylalkyl orhetaryl, B represents hydrogen, alkyl or alkoxyalkyl, or A and Btogether with the carbon atom to which they are attached represent asaturated or unsaturated unsubstituted or substituted cycle whichoptionally contains at least one heteroatom, D represents hydrogen or anoptionally substituted radical selected from the series consisting ofalkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl,saturated or unsaturated cycloalkyl in which one or more ring membersare optionally replaced by heteroatoms, arylalkyl, aryl, hetarylalkyl orhetaryl or A and D together with the atoms to which they are attachedrepresent a saturated or unsaturated cycle which is unsubstituted orsubstituted in the A,D moiety and which optionally contains at least one(in the case where CKE=(4)) further heteroatom, or A and Q¹ togetherrepresent alkanediyl or alkenediyl, each of which is optionallysubstituted by in each case optionally substituted alkyl, hydroxyl,alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl, or Q¹ representshydrogen or alkyl, Q², Q⁴, Q⁵ and Q⁶ independently of one another eachrepresent hydrogen or alkyl, Q³ represents hydrogen, alkyl, alkoxyalkyl,alkylthioalkyl, optionally substituted cycloalkyl (in which optionallyone methylene group is replaced by oxygen or sulphur) or optionallysubstituted phenyl, or Q³ and Q⁴ together with the carbon atom to whichthey are attached represent a saturated or unsaturated unsubstituted orsubstituted cycle which optionally contains a heteroatom, G representshydrogen (a) or represents one of the groups

 in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur, M represents oxygen or sulphur, R¹represents in each case optionally halogen-substituted alkyl, alkenyl,alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-,alkyl- or alkoxy-substituted cycloalkyl which may be interrupted by atleast one heteroatom, in each case optionally substituted phenyl,phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R² represents ineach case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl,polyalkoxyalkyl or represents in each case optionally substitutedcycloalkyl, phenyl or benzyl, R³, R⁴ and R⁵ independently of one anothereach represent in each case optionally halogen-substituted alkyl,alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthioand represent in each case optionally subsituted phenyl, benzyl, phenoxyor phenylthio, R⁶ and R⁷ independently of one another each representhydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl,alkenyl, alkoxy, alkoxyalkyl, represent optionally substituted phenyl,represent optionally substituted benzyl, or together with the nitrogenatom to which they are attached represent a cycle which is optionallyinterrupted by oxygen or sulphur.
 2. Compounds of the formula (I)according to claim 1 in which X represents halogen, C₁-C₆-alkyl,C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkoxy,C₃-C₆-halogenoalkenyloxy, nitro, cyano or in each case optionallyhalogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy,phenylthio, benzyloxy or benzylthio, Y represents one of the radicals

V¹ represents hydrogen, halogen, C₁-C₁₂-alkyl, C₁-C₆-alkoxy,C_(l)-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro, cyano or phenyl,phenoxy, phenoxy-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy,phenylthio-C₁-C₄-alkyl or phenyl-C₁-C₄-alkylthio, each of which isoptionally mono- or polysubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyano,V² and V³ independently of one another each represent hydrogen, halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl or C₁-C₄-halogenoalkoxy,Z represents hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl,C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy, nitro or cyano, CKE represents oneof the groups

A represents hydrogen or in each case optionally halogen-substitutedC₁-C₁₂-alkyl, C₃-C₈-alkenyl, C₁-C₁₀-alkoxy-C₁-C₈-alkyl,poly-C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₁₀-alkylthio-C₁-C₆-alkyl, optionallyhalogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl inwhich optionally one or two not directly adjacent ring members arereplaced by oxygen and/or sulphur or represents in each case optionallyhalogen-, C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkoxy-, cyano- or nitro-substituted C₆- or C₁₀-aryl,hetaryl having 5 to 6 ring atoms or C₆- or C₁₀-aryl-C₁-C₆-alkyl, Brepresents hydrogen, C₁-C₁₂-alkyl or C₁-C₈-alkoxy-C₁-C₆-alkyl or A, Band the carbon atom to which they are attached represent saturatedC₃-C₁₀-cycloalkyl or unsaturated C₅-C₁₀-cycloalkyl in which optionallyone ring member is replaced by oxygen or sulphur and which areoptionally mono- or disubstituted by C₁-C₈-alkyl, C₃-C₁₀-cycloalkyl,C₁-C₈-halogenoalkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, halogen or phenyl orA, B and the carbon atom to which they are attached representC₃-C₆-cycloalkyl which is substituted by an alkylenedilyl group whichoptionally contains one or two not directly adjacent oxygen and/orsulphur atoms, or by an alkylenedioxyl group or by an alkylenedithioylgroup which, together with the carbon atom to which it is attached,forms a further five- to eight-membered ring, or A, B and the carbonatom to which they are attached represent C₃-C₈-cycloalkyl orC₅-C₈-cycloalkenyl, in which two substituents together with the carbonatoms to which they are attached represent in each case optionallyC₁-C₆-alkyl-, C₁-C₆-alkoxy- or halogen-substituted C₂-C₆-alkanediyl,C₂-C₆-alkenediyl or C₄-C₆-alkanedienediyl in which optionally onemethylene group is replaced by oxygen or sulphur, D represents hydrogen,in each case optionally halogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₃-C₈-alkinyl, C₁-C₁₀-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,C₁-C₁₀-alkylthio-C₂-C₈-alkyl, optionally halogen-, C₁-C₄-alkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkyl-substituted C₃-C₈-cycloalkyl inwhich optionally one ring member is replaced by oxygen or sulphur or ineach case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano- or nitro-substitutedphenyl, hetaryl having 5 or 6 ring atoms, phenyl-C₁-C₆-alkyl orhetaryl-C₁-C₆-alkyl having 5 or 6 ring atoms, or A and D togetherrepresent in each case optionally substituted C₃-C₆-alkanediyl orC₃-C₆-alkenediyl in which optionally one methylene group is replaced byoxygen or sulphur,  possible substituents in each case being: halogen,hydroxyl, mercapto or in each case optionally halogen-substitutedC₁-C₁₀-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₃-C₇-cycloalkyl, phenyl orbenzyloxy, or a farther C₃-C₆-alkanediyl grouping, C₃-C₆-alkenediylgrouping or a butadienyl grouping which is optionally substituted byC₁-C₆-alkyl or in which optionally two adjacent substituents togetherwith the carbon atoms to which they are attached form a furthersaturated or unsaturated cycle having 5 or 6 ring atoms (in the case ofthe compound of the formula (I-1), A and D, together with the atoms towhich they are attached, then represent, for example, the groups AD-1 toAD-10 mentioned further below) which cycle may contain oxygen orsulphur, or which may optionally contain one of the groups below

A and Q¹ together represent C₃-C₆-alkanediyl or C₄-C₆-alkenediyl, eachof which is optionally mono- or disubstituted by identical or differentsubstituents elected from the group consisting of halogen, hydroxyl;C₁-C₁₀-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₃-C₇-cycloalkyl, each ofwhich is optionally mono- to trisubstituted by identical or differenthalogens; and benzyloxy and phenyl, each of which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of halogen, C₁-C₆-alkyl or C₁-C₆-alkoxy, and whichfurthermore optionally contains one of the groups below

 or is bridged by a C₁-C₂-alkanediyl group or by an oxygen atom, or Q¹represents hydrogen or C₁-C₄-alkyl, Q², Q⁴, Q⁵ and Q⁶ independently ofone another each represent hydrogen or C₁-C₄-alkyl, Q³ representshydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₂-alkyl,C₁-C₆-alkylthio-C₁-C₂-alkyl, optionally C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur or optionally halogen-,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, cyano- or nitro-substituted phenyl, or Q³ and Q⁴together with the carbon atom to which they are attached representoptionally C₁-C₄-alkyl-, C₁-C₄-alkoxy- orC₁-C₂-halogenoalkyl-substituted C₃-C₇-cycloalkyl in which optionally onering member is replaced by oxygen or sulphur, G represents hydrogen (a)or represents one of the groups

 in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur and M represents oxygen or sulphur, R¹ represents ineach case optionally halogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl,poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one ormore not directly adjacent ring members are replaced by oxygen and/orsulphur,  represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-, C₁-C₆-halogenoalkoxy-,C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl,  representsoptionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl,  represents optionally halogen- orC₁-C₆-alkyl-substituted 5- or 6-membered hetaryl,  represents optionallyhalogen- or C₁-C₆-alkyl-substituted phenoxy-C₁-C₆-alkyl or  representsoptionally halogen-, amino- or C₁-C₆-alkyl-substituted 5- or 6-memberedhetaryloxy-C₁-C₆-alkyl, R² represents in each case optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,  representsoptionally halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substitutedC₃-C₈-cycloalkyl or  represents in each case optionally halogen-,cyano-, nitro-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- orC₁-C₆-halogenoalkoxy-substituted phenyl or benzyl, R³ representsoptionally halogen-substituted C₁-C₈-alkyl or represents in each caseoptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl, R⁴and R⁵ independently of one another each represent in each caseoptionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio,C₂-C₈-alkenylthio, C₃-C₇-cycloalkylthio or represent in each caseoptionally halogen-, nitro-, cyano-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkyl- or C₁-C₄-halogenoalkyl-substituted phenyl, phenoxy orphenylthio, R⁶ and R⁷ independently of one another each representhydrogen, represent in each case optionally halogen-substitutedC₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, represent optionally halogen-,C₁-C₈-halogenoalkyl-, C₁-C₈-alkyl- or C₁-C₈-alkoxy-substituted phenyl,optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- orC₁-C₈-alkoxy-substituted benzyl or together represent an optionallyC₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally onecarbon atom is replaced by oxygen or sulphur, R¹³ represents hydrogen,represents in each case optionally halogen-substituted C₁-C₈-alkyl orC₁-C₈-alkoxy, represents optionally halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur, or represents in eachcase optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkoxy, R¹⁴ representshydrogen or C₁-C₈-alkyl, or R¹³ and R¹⁴ together representC₄-C₆-alkanediyl, R¹⁵ and R¹⁶ are identical or different and eachrepresent C₁-C₆-alkyl, or R¹⁵ and R¹⁶ together represent aC₂-C₄-alkanediyl radical which is optionally substituted by C₁-C₆-alkyl,C₁-C₆-halogenoalkyl or by optionally halogen-, C₁-C₆-alkyl-,C₁-C₄-halogenoalkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkoxy-, nitro- orcyano-substituted phenyl, R¹⁷ and R¹⁸ independently of one another eachrepresent hydrogen, represent optionally halogen-substituted C₁-C₈-alkylor represent optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, or R¹⁷ and R¹⁸ together with the carbon atom to which they areattached represent a carbonyl group or represent optionally halogen-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₅-C₇-cycloalkyl in whichoptionally one methylene group is replaced by oxygen or sulphur and R¹⁹and R²⁰ independently of one another each represent C₁-C₁₀-alkyl,C₂-C₁₀-alkenyl, C₁-C₁₀-alkoxy, C₁-C₁₀-alkylamino, C₃-C₁₀-alkenylamino,di-(C₁-C₁₀-alkyl)amino or di-(C₃-C₁₀-alkenyl)amino.
 3. Compounds of theformula (I) according to claim 1 in which. X represents fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, C₃-C₄-halogenoalkenyloxy,nitro or cyano, Y represents one of the radicals

V¹ represents hydrogen, fluorine, chlorine, bromine, C₁-C₆-alkyl,C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, nitro, cyano orphenyl, phenoxy, phenoxy-C₁-C₂-alkyl, phenyl-C₁-C₂-alkoxy,phenylthio-C₁-C₂-alkyl or phenyl-C₁-C₂-alkylthio, each of which isoptionally mono- or disubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,nitro or cyano, V² and V³ independently of one another each representhydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl or C₁-C₂-halogenoalkoxy, Z represents hydrogen,fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl,C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy, CKE represents one of the groups

A represents hydrogen, in each case optionally fluorine- orchlorine-substituted C₁-C₁-alkyl, C₁-C₈-alkoxy-C₁-C₆-alkyl, optionallyfluorine-, chlorine-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substitutedC₃-C₇-cycloalkyl in which optionally one ring member is replaced byoxygen or sulphur or (but not in the case of the compounds of theformulae (I-5), (I-7) and (I-8)) in each case optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-or C₁-C₄-halogenoalkoxy-substituted phenyl, furanyl, pyridyl,imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl, thienyl orphenyl-C₁-C₄-alkyl, B represents hydrogen or C₁-C₆-alkyl, or A, B andthe carbon atom to which they are attached represent saturated orunsaturated C₅-C₇-cycloalkyl in which optionally one ring member isreplaced by oxygen or sulphur and which is optionally mono-substitutedby C₁-C₆-alkyl, C₅-C₈-cycloalkyl, C₁-C₃-halogenoalkyl, C₁-C₆-alkoxy,fluorine, chlorine or phenyl, or A, B and the carbon atom to which theyare attached represent C₅-C₆-cycloalkyl which is substituted by analkylenediyl group which optionally contains one or two not directlyadjacent oxygen or sulphur atoms or by an alkylenedioxyl group or by analkylenedithiol group which, together with the carbon atom to which itis attached, forms a further five- or six-membered ring, or A, B and thecarbon atom to which they are attached represents C₃-C₆-cycloalkyl orC₅-C₆-cycloalkenyl in which two substituents together with the carbonatoms to which they are attached represent in each case optionallyC₁-C₅-alkyl-, C₁-C₅-alkoxy-, fluorine-, chlorine- or bromine-substitutedC₂-C₄-alkanediyl, C₂-C₄-alkenediyl, in which optionally one methylenegroup is replaced by oxygen or sulphur, or butadienediyl, D representshydrogen, represents in each case optionally fluorine- orchlorine-substituted C₁-C₁l-alkyl, C₃-C₆-alkenyl,C₁-C₈-alkoxy-C₂-C₆-alkyl or C₁-C₈-alkylthio-C₂-C₆-alkyl, representsoptionally fluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy- orC₁-C₂-halogenoalkyl-substituted C₃-C₇-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur or (but not in the caseof the compounds of the formulae (I-1) and (I-4)) represents in eachcase optionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substitutedphenyl, furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl,pyrrolyl, thienyl, triazolyl or phenyl-C₁-C₄-alkyl, or A and D togetherrepresent optionally substituted C₃-C₅-alkanediyl in which one methylenegroup may be replaced by a carbonyl group, oxygen or sulphur, possiblesubstituents being hydroxyl, C₁-C₆-alkyl or C₁-C₄-alkoxy, or A and D (inthe case of the compounds of the formula (I-1)) together with the atomsto which they are attached represent one of the groups AD-1 to AD-10:

A and Q¹ together represent C₃-C₄-alkanediyl or C₃-C₄-alkenediyl, eachof which is optionally mono- or disubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,hydroxyl, and C₁-C₈-alkyl and C₁-C₄-alkoxy, each of which is optionallymono- to trisubstituted by fluorine, or Q¹ represents hydrogen, Q²represents hydrogen, Q⁴, Q⁵ and Q⁶ independently of one another eachrepresent hydrogen or C₁-C₃-alkyl, Q³ represents hydrogen, C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl or optionallymethyl- or methoxy-substituted C₃-C₆-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur, or Q³ and Q⁴ togetherwith the carbon atom to which they are attached represent an optionallyC₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted saturated C₅-C₆-cycloalkyl inwhich optionally one ring member is replaced by oxygen or sulphur, Grepresents hydrogen (a) or represents one of the groups

 in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur and M represents oxygen or sulphur, R¹ represents ineach case optionally fluorine- or chlorine-substituted C₁-C₁₆-alkyl,C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl,poly-C₁-C₆-alkoxy-C₁-C₆-alkyl or optionally fluorine-, chlorine-,C₁-C₅-alkyl- or C₁-C₅-alkoxy-substituted C₃-C₇-cycloalkyl in whichoptionally one or two not directly adjacent ring members are replaced byoxygen and/or sulphur,  represents optionally fluorine-, chlorine-,bromine-, cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₃-halogenoalkyl-, C₁-C₃-halogenoalkoxy-, C₁-C₄-alkylthio- orC₁-C₄-alkylsulphonyl-substituted phenyl,  represents optionallyfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₃-halogenoalkyl- or C₁-C₃-halogenoalkoxy-substitutedphenyl-C₁-C₄-alkyl,  represents in each case optionally fluorine-,chlorine-, bromine- or C₁-C₄-alkyl-substituted pyrazolyl, thiazolyl,pyridyl, pyrimidyl, furanyl or thienyl,  represents optionallyfluorine-, chlorine-, bromine- or C₁-C₄-alkyl-substitutedphenoxy-C₁-C₃-alkyl or  represents in each case optionally fluorine-,chlorine-, bromine-, amino- or C₁-C₄-alkyl-substitutedpyridyloxy-C₁-C₃-alkyl, pyrimidyloxy-C₁-C₃-alkyl orthiazolyloxy-C₁-C₃-alkyl, R² represents in each case optionallyfluorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₂-C₆-alkyl or poly-C₁-C₆-alkoxy-C₂-C₆-alkyl,  representsoptionally fluorine-, chlorine-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl or  represents in each caseoptionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-,C₁-C₃-alkoxy-, C₁-C₃-halogenoalkyl- or C₁-C₃-halogenoalkoxy-substitutedphenyl or benzyl, R³ represents optionally fluorine-substitutedC₁-C₆-alkyl or represents in each case optionally fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl-,C₁-C₃-halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl, R⁴and R⁵independently of one another each represent C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,C₃-C₄-alkenylthio, C₃-C₆-cycloalkylthio or represent in each caseoptionally fluorine-, chlorine-, bromine-, nitro-, cyano-,C₁-C₃-alkoxy-, C₁-C₃-halogenoalkoxy-, C₁-C₃-alkylthio-,C₁-C₃-halogenoalkylthio-, C₁-C₃-alkyl- orC₁-C₃-halogenoalkyl-substituted phenyl, phenoxy or phenylthio, and R⁶and R⁷ independently of one another each represent hydrogen,C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl,C₁-C₆-alkoxy-C₁-C₆-alkyl, represent optionally fluorine-, chlorine-,bromine-, C₁-C₃-halogenoalkyl-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substitutedphenyl, represent optionally fluorine-, chlorine-, bromine-,C₁-C₄-alkyl-, C₁-C₃-halogenoalkyl- or C₁-C₄-alkoxy-substituted benzyl,or together represent an optionally methyl- or ethyl-substitutedC₄-C₅-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur.
 4. Compounds of the formula (I) accordingto claim 1 in which X represents fluorine, chlorine, methyl, ethyl,propyl, iso-propyl, methoxy, ethoxy, propoxy, iso-propoxy,trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano, Yrepresents one of the radicals

V¹ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, methoxy, ethoxy,n-propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy, nitro, cyanoor phenyl, V² and V³ independently of one another each representhydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl,methoxy, ethoxy, trifluoromethyl or trifluoromethoxy, Z representshydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, methoxy, ethoxyor n-propoxy, CKE represents one of the groups

A represents hydrogen, in each case optionally fluorine-substitutedC₁-C₈-alkyl or C₁-C₆-alkoxy-C₁-C₄-alkyl, optionally fluorine-, methyl-,ethyl- or methoxy-substituted C₃-C₆-cycloalkyl in which optionally onering member is replaced by oxygen or sulphur or (but not in the case ofthe compounds of the formulae (I-5), (I-7) and (I-8)) represents in eachcase optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-,n-propyl-, iso-propyl-, methoxy-, ethoxy-, trifluoromethyl-,trifluoromethoxy-, cyano- or nitro-substituted phenyl or benzyl, Brepresents C₁-C₄-alkyl, or A, B and the carbon atom to which they areattached represent saturated C₅-C₆-cycloalkyl in which optionally onering member is replaced by oxygen or sulphur and which is optionallymonosubstituted by methyl, ethyl, n-propyl, isopropyl, butyl, iso-butyl,sec-butyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, n-propoxy,iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy, fluorine orchlorine, or A, B and the carbon atom to which they are attachedrepresent C₅-C₆-cycloalkyl in which two substituents together with thecarbon atoms to which they are attached represent C₂-C₄-alkanediyl orC₂-C₄-alkenediyl in which in each case optionally one methylene group isreplaced by oxygen or sulphur, or, butadienediyl, D represents hydrogen,represents in each case optionally fluorine- or chlorine-substitutedC₁-C₈-alkyl, C₃-C₄-alkenyl, C₁-C₆-alkoxy-C₂-C₄-alkyl,C₁-C₄-alkylthio-C₂-C₄-alkyl or C₃-C₆-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur or (but not in the caseof the compounds of the formulae (I-1) and (I4)) represents in each caseoptionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-,iso-propyl-, methoxy-, ethoxy-, trifluoromethyl- ortrifluoromethoxy-substituted phenyl, furanyl, pyridyl, thienyl orbenzyl, or A and D together represent optionally substitutedC₃-C₄-alkanediyl in which optionally one carbon atom is replaced bysulphur and which is optionally substituted by hydroxyl, methyl, ethyl,methoxy or ethoxy, or A and D (in the case of the compounds of theformula (I-1)) together with the atoms to which they are attachedrepresent one of the following groups AD:

A and Q¹ together represent C₃-C₄-alkanediyl or butenediyl, each ofwhich is optionally mono- or disubstituted by fluorine, hydroxyl, methylor methoxy, or Q¹ represents hydrogen, Q² represents hydrogen, Q⁴, Q⁵and Q⁶ independently of one another each represent hydrogen, methyl orethyl, Q³ represents hydrogen, methyl, ethyl or C₃-C₆-cycloalkyl inwhich optionally one methylene group is replaced by oxygen or sulphur,or Q³ and Q⁴ together with the carbon atom to which they are attachedrepresent optionally methyl- or methoxy-substituted saturatedC₅-C₆-cycloalkyl in which optionally one ring member is replaced byoxygen or sulphur, G represents hydrogen (a) or represents one of thegroups

 in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur and M represents oxygen or sulphur, R¹ represents ineach case optionally fluorine- or chlorine-substituted C₁-C₁₄-alkyl,C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₁-C₆-alkyl, C₁-C₄-alkylthio-C₁-C₆-alkyl;poly-C₁-C₄-alkoxy-C₁-C₄-alkyl or optionally fluorine-, chlorine-,methyl-, ethyl-, n-propyl-, i-propyl-, n-butyl-, i-butyl-, tert-butyl-,methoxy-, ethoxy-, n-propoxy- or iso-propoxy-substitutedC₃-C₆-cycloalkyl in which optionally one or two not directly adjacentring members are replaced by oxygen and/or sulphur,  representsoptionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-,ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl-,trifluoromethoxy-, methylthio-, ethylthio-, methylsulphonyl- orethylsulphonyl-substituted phenyl,  represents optionally fluorine-,chlorine-, bromine-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-,ethoxy-, trifluoromethyl- or trifluoromethoxy-substituted benzyl, represents in each case optionally fluorine-, chlorine-, bromine-,methyl- or ethyl-substituted furanyl, thienyl, pyridyl, pyrimidyl,thiazolyl or pyrazolyl,  represents optionally fluorine-, chlorine-,methyl- or ethyl-substituted phenoxy-C₁-C₂-alkyl or  represents in eachcase optionally fluorine-, chlorine-, amino-, methyl- orethyl-substituted pyridyloxy-C₁-C₂-alkyl, pyrimidyloxy-C₁-C₂-alkyl orthiazolyloxy-C₁-C₂-alkyl, R² represents in each case optionallyfluorine-substituted C₁-C₁₄-alkyl, C₂-C₁₄-alkenyl,C₁-C₄-alkoxy-C₂-C₆-alkyl or poly-C₁-C₄-alkoxy-C₂-C₆-alkyl,  representsoptionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, iso-propyl-or methoxy-substituted C₃-C₆-cycloalkyl,  or represents in each caseoptionally fluorine-, chlorine-, cyano-, nitro-, methyl-, ethyl-,n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- ortrifluoromethoxy-substituted phenyl or benzyl, R³ represents in eachcase optionally fluorine-substituted methyl, ethyl, n-propyl, isopropylor in each case optionally fluorine-, chlorine-, bromine-, methyl-,tert-butyl-, methoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- ornitro-substituted phenyl or benzyl, R⁴ and R⁵ independently of oneanother each represent C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,di-(C₁-C₄-alkyl)amino, C₁-C₄-alkylthio or represent in each caseoptionally fluorine-, chlorine-, bromine-, nitro-, cyano-,C₁-C₂-alkoxy-, C₁-C₂-fluoroalkoxy-, C₁-C₂-alkylthio-,C₁-C₂-fluoroalkylthio- or C₁-C₃-alkyl-substituted phenyl, phenoxy orphenylthio, and R⁶ and R⁷ independently of one another each representhydrogen, represent C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy,C₃-C₄-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, represent optionally fluorine-,chlorine-, bromine-, trifluoromethyl-, methyl- or methoxy-substitutedphenyl, represent optionally fluorine-, chlorine-, bromine-, methyl-,trifluoromethyl- or methoxy-substituted benzyl, or together represent aC₅-C₆-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur.
 5. Process for preparing compounds of theformula (I) according to claim 1, characterized in that (A) Compounds ofthe formula (I-1-a)

 in which A, B, D, X, Y and Z are each as defined in claim 1 areobtained by the intramolecular condensation of N-acylamino acid estersof the formula (II)

 in which A, B, D, X, Y and Z are each as defined above, and R⁸represents alkyl, in the presence of a diluent and in the presence of abase, (B) Compounds of the formula (I-2-a)

 in which A, B, X, Y and Z are each as defined above, are obtained bythe intramolecular condensation of carboxylic esters of the formula(III)

 in which A, B, X, Y, Z and R⁸ are each as defined above, in thepresence of a diluent and in the presence of a base, (C) Compounds ofthe formula (I-3-a)

 in which A, B, X, Y and Z are each as defined above, are obtained bythe intramolecular cyclization of β-ketocarboxylic esters of the formula(IV)

 in which A, B, X, Y, Z and R⁸ are each as defined above and Wrepresents hydrogen, halogen, alkyl or alkoxy, if appropriate in thepresence of a diluent and in the presence of an acid, (D) Compounds ofthe formula (I-4-a)

 in which A, D, X, Y and Z are each as defined above, are obtained byreacting (α) halogenocarbonyl ketenes of the formula (V)

 in which X, Y and Z are each as defined above and Hal representshalogen, or by reacting (β) malonic acid derivatives of the formula (VI)

 in which R⁸, X, Y and Z are each as defined above, with hydrazines ofthe formula (VII) A-NH—NH-D  (VII)  in which A and D are each as definedabove, if appropriate in the presence of a diluent and if appropriate inthe presence of a base, (E) Compounds of the formula (I-5-a)

 in which A, D, X, Y and Z are each as defined above, are obtained byreacting carbonyl compounds of the formula (VIII)

 in which A and D are each as defined above, or their silyl enol ethersof the formula (VIIIa)

 in which A, D and R⁸ are each as defined above, with ketene acidhalides of the formula (V)

 in which X, Y and Z are each as defined above and Hal representshalogen, if appropriate in the presence of a diluent and if appropriatein the presence of an acid acceptor, (F) Compounds of the formula(I-6-a)

 in which A, X, Y and Z are each as defined above, are obtained byreacting thioamides of the formula (IX)

 in which A is as defined above, with ketene acid halides of the formula(V)

 in which Hal, X, Y and Z are each as defined above, if appropriate inthe presence of a diluent and if appropriate in the presence of an acidacceptor, (G) Compounds of the formula (I-7-a)

 in which A, B, Q¹, Q², W, X, Y and Z are each as defined in claim 1 areobtained by intramolecular cyclization of ketocarboxylic esters of theformula (X)

 in which A, B, Q¹, Q², X, Y and Z are each as defined above and R⁸represents alkyl, if appropriate in the presence of a diluent and in thepresence of a base, (H) Compounds of the formula (I-8-a)

 in which A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined in claim1 are obtained by intramolecular condensation of 6-aryl-5-keto-hexanoicesters of the formula (XI)

 in which A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above andR⁸ represents alkyl, in the presence of a diluent and in the presence ofa base, (I) Compounds of the formulae (I-8-a) shown above in which A, B,D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above areobtained by reacting compounds of the formulae (I-1′-a) to (I-8′-a),

 in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X and Z are each as definedabove and Y′ presents chlorine, bromine or iodine with boronic acids ofthe formula (XII)

 in which Y is as defined above, in the presence of a solvent, a baseand a catalyst and subsequently reacting the resulting compounds of theformulae (I-1-a) to (I-8-a) in each case (Jα) with acyl halides of theformula (XIII)

 in which R¹ is as defined in claim 1 and Hal represents halogen or (β)with carboxylic anhydrides of the formula (XIV) R¹—CO—O—CO—R¹  (XIV)  inwhich R¹ is as defined above, if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder, or in eachcase (K) with chloroformic esters or chloroformic thioesters of theformula (XV) R²-M-CO—Cl  (XV)  in which R² and M are each as defined inclaim 1, if appropriate in the presence of a diluent and if appropriatein the presence of an acid binder, or in each case (L) withchloromonothioformic esters or chlorodithioformic esters of the formula(XVI)

 in which M and R² are each as defined above, if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder, or in each case (M) with sulphonyl chlorides of the formula(XVII) R³—SO₂—Cl  (XVII)  in which R³ is as defined in claim 1, ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder, or in each case (N) with phosphoruscompounds of the formula (XVIII)

 in which L, R⁴ and R⁵ are each as defined in claim 1 and Hal representshalogen, if appropriate in the presence of a diluent and if appropriatein the presence of an acid binder, or in each case (L) with metalcompounds or amines of the formulae (XIX) or (XX)

 in which Me represents a mono- or divalent metal, t represents thenumber 1 or 2 and R¹⁰, R¹¹, R¹² independently of one another eachrepresent hydrogen or alkyl, if appropriate in the presence of adiluent, or in each case (Pα) with isocyanates or isothiocyanates of theformula (XXI) R⁶—N═C═L  (XXI)  in which R⁶ and L are each as defined inclaim 1, if appropriate in the presence of a diluent and if appropriatein the presence of a catalyst, or in each case (β) with carbamoylchlorides or thiocarbamoyl chlorides of the formula (XXII)

 in which L, R⁶ and R⁷ are each as defined in claim 1, if appropriate inthe presence of a diluent and if appropriate in the presence of an acidbinder.
 6. Compounds of the formula (II)

in which A, B, D, X, Y and Z are each as defined in claim 1 and R⁸represents alkyl.
 7. Compounds of the formula (XXIV)

in which X, Y and Z are each as defined in claim 1 and Hal representschlorine or bromine.
 8. Compounds of the formula (XXV)

in which A, B, D, X, Y and Z are each as defined in claim
 1. 9.Compounds of the formula (XXIX)

in which A, B, D, X, Y and Z are each as defined in claim
 1. 10.Compounds of the formula (III)

in which A, B, X, Y and Z are each as defined above and R⁸ representsalkyl.
 11. Compounds of the formula (XXVII)

in which X, Y and Z are each as defined in claim
 1. 12. Compounds of theformula (XXXII)

in which X, Y and Z are each as defined in claim 1 and R⁸ representsalkyl.
 13. Compounds of the formula (XXVII-b)

in which X and Z are each as defined in claim
 1. 14. Compounds of theformula (IV)

in which A, B, W, X, Y and Z are each as defined in claim 1 and R⁸represents alkyl.
 15. Compounds of the formula (V)

in which X, Y and Z are each as defined in claim 1 and Hal representschlorine or bromine.
 16. Compounds of the formula (XXXVII)

in which X, Y and Z are each as defined in claim
 1. 17. Compounds of theformula (VI)

in which X, Y and Z are each as defined in claim 1 and R⁸ representsalkyl.
 18. Compounds of the formula (X)

in which A, B, Q¹, Q², X, Y and Z are each as defined in claim 1 and R⁸represents alkyl.
 19. Compounds of the formula (XXXVIII)

in which X, Y, Z, A, B, Q¹ and Q² are each as defined in claim
 1. 20.Compounds of the formula (XXXIX)

in which A, B, D¹, D², X, Y and Z are each as defined in claim 1 and R⁸and R^(8′) each represent alkyl.
 21. Compounds of the formula (XI)

in which A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined in claim 1and R⁸ represents alkyl.
 22. Compounds of the formula (XLII)

in which A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined inclaim
 1. 23. Compounds of the formula (XLIII)

in which A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined in claim 1and R⁸ and R^(8′) each represent alkyl.
 24. Pesticides and/orherbicides, characterized in that they contain at least one compound ofthe formula (I) according to claim
 1. 25. The use of compounds of theformula (I) according to claim 1 for controlling pests in cropprotection, in the domestic sector, in the hygiene sector and in theprotection of stored products.
 26. Method for controlling pests in cropprotection, in the domestic sector, in the hygiene sector and in theprotection of stored products, characterized in that compounds of theformula (I) according to claim 1 are allowed to act on the pests and/ortheir habitat.
 27. Method for preparing pesticides and/or herbicides,characterized in that compounds of the formula (I) according to claim 1are mixed with extenders and/or surfactants.